bluuebunny/crossref_metadata_2025 huggingface dataset:
Recycling Is Not Enough
Authors: Steinberg Paul F.
Published: November 2020

Faced with an endless stream of alarming news about the environment—rising temperatures and declining water supplies, population growth and species extinction, oil spills and cancer clusters—people increasingly want to know what can actually be done to address these problems. Concerned parents comb through websites late at night in search of safer products for their children. Students pack lecture halls in hundreds of environmental studies programs that have popped up on college campuses across the globe. Our grocery aisles and magazine stands are filled with advertisements promising that sustainability is just one more purchase around the corner. The major current of environmental thinking today emphasizes the small changes we can make as individuals, which (we are told) will add up to something big. Michael Maniates, a political scientist at Allegheny College, observes that the responsibility for confronting these issues too often “falls to individuals, acting alone, usually as consumers.” Yet solutions that promote green consumerism and changes in personal lifestyles strike many of us as strangely out of proportion with enormous problems like climate change, urban air pollution, and the disappearance of tropical forests. We learn that glaciers are melting and sea levels are expected to rise due to global warming—and in response we are advised to ride a bicycle to work. Scientists tell us that one out of every five mammal species in the world is threatened with extinction, and we react by switching coffee brands. Is it any wonder that people despair that real solutions are not within their grasp? You may suspect that tackling these gargantuan problems will require something more—but what? The answer, it turns out, can be found in a mountain of books and research articles published by thousands of social scientists over the past quarter century. But their discoveries have remained largely hidden from public view.
The Big Trade
Authors: Steinberg Paul F.
Published: November 2020

As we continue our exploration of who rules the earth, we find that the economy, once you look inside it, relies on a vast system of rules and regulations, its cogs and wheels spinning day and night to enable the countless transactions that make up a modern economy. The relation between markets and rules is a fascinating one, far more complex than is suggested by the usual debates over government regulation versus free enterprise. Markets rely on rules. But increasingly, the reverse is also true: Some of our most innovative environmental policies and regulations have embedded within them market incentives designed to promote pro-environment behavior. To appreciate the stakes, let’s begin by considering what is arguably the greatest environmental tragedy—and biggest environmental success story—of all time. The removal of tetraethyl lead from gasoline has had a profound impact on human health and well-being worldwide. The change began in the United States in the late 1970s, soon spread to Europe, and over the next two decades diffused throughout the entire world. This shift was prompted by an innovative set of rules that actually assigned property rights to poison—and in the process created incentives for widespread changes in corporate behavior. Under the Clean Air Act of 1970, the US Environmental Protection Agency had the legal authority to regulate tetraethyl lead, which had been added to gasoline since the 1920s to boost engine performance. The original decision to add “ethyl” to the chemical mixture sloshing around in our gas tanks took place despite dire warnings from health experts. Foremost among these was Alice Hamilton, Harvard’s first female professor and the country’s leading expert on the health impacts of lead, which she knew intimately from her studies of worker exposure in the largely unregulated “dangerous trades” of the time. In 1925, the US Surgeon General convened a special meeting to decide whether ethyl production could proceed despite the known health risks. Hamilton argued that it would be reckless to deliberately disperse throughout the air a substance whose toxic effects (notably damage to the human nervous system) were well known for centuries.
Venturing Out: The Irish Wilderness and Columba of Iona
Authors: Lane Belden C.
Published: November 2020

I put in at Greer Crossing, planning to float the twenty-one miles to Riverton over the next three days. Canoeing the Eleven Point River—a National Wild and Scenic Riverway near the Arkansas border—is a quintessential Ozark experience. The stream skirts the western boundary of the Irish Wilderness, a 16,500-acre area of the National Wilderness system. It’s a pocket of dense forest, sparkling creeks, and limestone caves as wild as the wooded glens of Ireland’s Wicklow Mountains. The place abounds with white-tailed deer, bobcats, raccoons, gray foxes, brown trout, and songbirds galore. A Celtic mystery lurks in this secluded Missouri landscape. I like to think of the Irish Wilderness as connecting me with my family roots in Ireland and Cornwall, near Land’s End in southwest England. It takes me back to a spiritual practice of wilderness wandering firmly rooted in the Celtic tradition. The Druids would have loved this part of southern Missouri. A dozen species of oak spread their branches overhead. Colonies of mayapples thrive along the trail. The limestone bluffs above the river are scattered with dolomite crystals. Canoeing downstream, you hear the sound of a beaver tail slapping the water to warn its kits as you round a bend. Ducking under the branches of an overhanging sycamore tree, you’re surprised by a harmless rat snake resting on a limb. With each stroke, the paddle dips into crystal-clear water rising from underground springs. There are times in your life when you realize you need a discipline. You have to decide about where you’re going (or not going). That’s why I’m here—to renew a spiritual regimen in my life, venturing out so as to find my way back in again. Salmon do it instinctively as a part of their life cycle, swimming upstream to their source. Naturalist Freeman House says that humans and salmon are a lot alike: “We are related by virtue of the places to which we choose to return.” I, too, need to revert from time to time to the primeval wonders of great blue herons and hazelnut trees . . . to an untamed Celtic landscape.
Failure: Mt. Whitney and Martin Luther
Authors: Lane Belden C.
Published: November 2020

There are times on the trail when you have to turn back. Nothing is more discouraging. Maybe you’ve done something stupid, like losing the map. Changing weather conditions may have made it dangerous or foolhardy to go any further. Maybe your gear is soaking wet or the black flies have become unbearable. Sometimes you simply don’t have it in you to go on. Whatever brings you to that point, you admit defeat and grudgingly head back toward the trailhead. Yet there are times when not reaching one’s goal on a pack trip may be even better than having done so. At least that’s what I’ve always told myself about my failure to climb Mt. Whitney. It was my second year at seminary in California. My roommate Eric and I wanted to cap off our previous trips into the Sierra Nevada by hiking the highest peak in the lower forty-eight. We had made mistakes on earlier hikes, as we would on this one. That’s always easy to do in the Sierras. One afternoon on an earlier trip, for instance, we’d been returning to our base camp on the High Sierra Trail when we got tired of the interminable switchbacks. We decided to take a “shortcut” down through the rocks. But within ten minutes we were in trouble, facing a level of rock-climbing for which we weren’t prepared. We soon were separated, each of us fearing the other had fallen as we heard rock tumbling in the distance, then nothing but silence. Hours later we stumbled onto each other on the trail in the dark far below, grateful to be alive—knowing how foolish we had been. That’s what wilderness does for you, says Gary Snyder. It lets you make all the mistakes you need in order to get where you’re really going. The trail we took up Mt. Whitney, peaking at 14,505 feet, was a grueling one. The average elevation gain is 550 feet a mile, though the altitude makes it seem twice that. But the beauty is incredible. Hidden lakes appear and disappear on the winding trail.
Discernment: Taum Sauk Mountain and Jelaluddin Rumi
Authors: Lane Belden C.
Published: November 2020

Four hundred million years ago, Taum Sauk Mountain was a high ridge on a solitary island in a vast Paleozoic sea surrounded by coral reefs. Geologists describe it as a landscape of lofty volcanoes. It was one of the few parts of present-day North America that were never submerged under a primordial sea. At 1,772 feet above sea level, Taum Sauk Mountain has been worn down through the ages but is still the highest point in Missouri. It lies on the crest of a mountain chain several times older than the Appalachians. The Taum Sauk section of the Ozark Trail is one of the most beautiful stretches in the Ozarks. The twelve-and-a-half-mile tract that runs from the blue pools and massive boulders of Johnson’s Shut-Ins State Park to the top of Taum Sauk Mountain is studded with waterfalls, thick woodlands, rocky glades, and beaver ponds. It is a good place for reflecting on primeval things, gaining a long-range perspective on one’s life, discerning what has gone and what may yet need to come. This is one of the boons of wilderness hiking. Turning onto route CC off Highway 21 in Iron County on a Friday afternoon, I’ve made it to the top of the mountain a few hours before dark. My plan is to hike down the trail below Mina Sauk Falls, spending the night in the woods near Devil’s Tollgate and moving on toward Johnson’s Shut-ins the next day. I’ve come to an intriguing place. In wet weather, the water cascades 132 feet down rock ledges, forming the highest waterfall in the state. Below the falls the trail passes through an eight-foot-wide opening in a thirty-foot-deep section of magma that was part of an ancient volcanic caldera. Hardened now into fine-grained rhyolite, the geological oddity is dubbed the Devil’s Tollgate. A pioneer wagon road once passed between its stone walls, making a convenient site for bandits to hide. The locals claim that Jesse James hid out on the mountain after robbing the Ironton Train in 1874. Until the State Park System built a road to its top in the 1950s, Taum Sauk Mountain was a remote and isolated place.
Holy Folly: Aravaipa Canyon and Thomas Merton
Authors: Lane Belden C.
Published: November 2020

The trip didn’t make sense at the time. Most backpacking trips don’t. There are always more pressing things to do. We didn’t have the time or the money, but we went anyway. Sometimes you just gotta drive to the end of a long dirt road in the middle of the desert and keep walking. When Aravaipa Canyon lies at the end of that road, you know you won’t be disappointed. Mike and I had come to southeastern Arizona to hike the twelve-mile length of the Aravaipa Canyon Wilderness Area. “Laughing Waters” is the name the Apaches gave to the site. The Aravaipa band of the Western Apache lived here in the nineteenth century. They did well at first—hunting deer in the side canyons; gathering saguaro fruit, mesquite beans, and pinyon nuts; catching native fish that thrived in the creek. But by the 1870s, drought drove them out. When they sought relief at Camp Grant a few miles away a Tucson mob organized a massacre that left them decimated. The government relocated the remainder of the tribe in the White Mountain Reservation to the north. These canyon walls, reaching a thousand feet high in places, hold memories of children playing under reddish-brown hoodoos and dark stories etched in the desert varnish of the rock. Today the Bureau of Land Management regulates entry into the canyon, limiting permits to thirty hikers a day at the western entrance. For much of the way you slog through ankle- to knee-deep water, stopping at every bend to marvel at what rises before you. Towering red cliffs, stands of green willows and cottonwoods, jimson weed and desert marigolds, cactuses of every sort. This is a place where humans are outnumbered by bighorn sheep, where poisonous centipedes hide in thick grass, and serpentine side canyons darken ominously in the late afternoon sun. I’ve loved it since I first set eyes on it. At the start of this book I mentioned a night I’d spent alone in the desert near here a few years earlier. What I experienced that night would finally make sense on this subsequent trip into the canyon proper.
Introduction
Authors: Nadeau Robert
Published: November 2020

In the house that seems embarrassingly large and mostly empty now that our children are grown and have children of their own, there is a screened-in porch adjacent to the family room on the second floor. When my wife and I sit on this porch during the summer, after the leaves on the old growth trees in our back yard open and many varieties of birds magically appear, it seems, for a moment at least, that all is right with the world. Laurel oaks and Virginia pines tower over a landscape covered in a canopy of intense green leaves, and members of two families of gray squirrels perform acrobatic feats in the maze of limbs and branches. American goldfinch with bright yellow bodies and black wings, northern cardinals with red bodies and orange bills, and pileated woodpeckers with large red crests and moustaches are frequent visitors. After evening comes and the sky begins to grow dark, the magical mystery tour continues as deer and the occasional lone fox or coyote pass through the thick foliage in the woods behind the house. But when we sat on this porch during the summer of 2010, it was not possible to feel even for a moment that all was right with the world. The outside temperature was oppressively hot for most of the day, and there were record-breaking heat waves across the United States, Europe, and Asia. The temperature in South Central Pakistan in May was the highest ever recorded in Asia, 128 degrees Fahrenheit, and the average temperature in Moscow in July was an unprecedented 100 degrees Fahrenheit. In August, scientists at the World Meteorological Organization (WMO) said that research based on enhanced climate models indicated that global warming was responsible for these much higher than average temperatures. The scientists at WMO also concluded that higher temperatures in the Atlantic Ocean and atmospheric anomalies caused by a La Nina created conditions that resulted in the severe draught in Russia, the flooding and mudslides in western China, and the floods that inundated about one-fifth of the landmass in Pakistan.
Rebirth of the Sacred : Science, Religion, and the New Environmental Ethos
Authors: Nadeau Robert
Published: November 2020

In the dream of earth, Thomas Berry makes the following comment about the environmental crisis: “It’s all a question of story. We are in trouble now because we do not have a good story. We are in between stories. The old story, the account of how the world came to be and how we fit into it, is no longer effective.” The intent in this book is to tell the new story that could greatly enhance the prospect of resolving the environmental crisis. One of the frame tales for this story is science. On the most obvious level, scientific knowledge has gifted us with an understanding of the causes of this crisis and how it can be resolved. What is not so obvious is that this knowledge has also revealed that the old stories about political and economic reality are badly in need of revision. The old story is imaged on the conventional globes that sit in classrooms, government offices, libraries, and home offices like the one in which I am writing this book. On these globes, boundaries between nation-states are marked with dark lines, and the regions or territories governed by these states are painted different primary colors. The parts (nation-states) are separate and discrete entities, the whole (planet earth) is static, and the sum of the parts constitutes the whole. In the geopolitical reality imaged on these globes, seven billion people live within the borders of sovereign nation-states and construct their identities based on diverse cultural narratives about nationalism, ethnicity, political ideology, and religious beliefs and practices. The only source of political power in this reality is the sovereign nation-state, and these states endlessly compete with one another for the capital and scarce natural resources needed to sustain and grow their national economies. The new story is imaged in the digital photographs and videos taken by earth-orbiting satellites that environmental scientists use to study the complex web of interactions between human and environmental systems.
The New Story in Physics: Mind, Matter, and the Nonlocal Universe
Authors: Nadeau Robert
Published: November 2020

The capacity to acquire and use fully complex language systems made the members of our species fully conscious and self-aware beings in the vast cosmos. But this enormous privilege came with a price. After our ancestors began to live storied lives in a linguistically based symbolic universe, the world that previous generations experienced as an integrated and undivided whole split into two worlds—an inner world where the self that is aware of its own awareness exists and an outer world in which this self seeks to gratify its needs and establish a meaningful sense of connection with other selves. And this explains why the most fundamental impulse in the storied lives of fully modern humans has always been to close the gap between these inner and outer worlds by integrating all seemingly discordant parts of a symbolic universe into a meaningful and coherent whole. The narrative that has consistently served this function is religion. But during the first scientific revolution of the seventeenth century, another narrative emerged called Newtonian or classical physics that also promised to bridge the gap between self and world by integrating all of the seemingly discordant parts of the physical universe into a coherent and meaningful whole. In this physics, one universal force, gravity, governs the motion, interaction, and blending of indestructible atoms or mass points. And since the laws of gravity were completely deterministic, it was assumed that all events in the cosmos are predetermined by the forces associated with these laws and that the future of any physical system could be predicted with absolute certainty if initial conditions are known. In the worldview of classical physics, human beings were cogs in a giant machine and linked to other parts of this machine in only the most mundane material terms. The knowing self was separate, discrete, and isolated from the physical world, and all the creativity of the cosmos was exhausted in the first instant of creation. As physicist Henry Stapp points out, “Classical physics not only fails to demand the mental, it fails to even provide a rational place for the mental.
Nerves Redux
Authors: Shorter Edward
Published: November 2020

We might have thought that the concept of nerves ended in 1957 when the United States Post Office Department initiated a fraud proceeding against John Winters of New York City, who had been promoting a product called Orbacine containing bromide and niacin for “every-day nervousness and its symptoms.” Although Winters’ claims went a bit beyond nerves, the Post Office wanted an end to the whole business and Orbacine disappeared. But the concept of nerves had enemies other than the Post Office. Three in particular had tried to do away with it: psychoanalysis, psychopharmacology, and the DSM series. All failed to kill it completely, and the concept lingers on because of its obvious face value: Our patients clearly have a nervous illness or something resembling it. They do not have a “mood disorder.” In medicine the nervous syndrome, the condition that dare not speak its name, has taken on various allures. Once upon a time, hysteria was the equivalent of a nervous diagnosis in women. There were physicians who had little patience with calling their former hysteric patients “depressed”: They remained hysteric! Jacques Frei, a member of the department of psychiatry of the University of Lausanne in Switzerland, noted in 1984 “the importance that depressive symptomatology has taken today as a call for help among female hysterics. . . . It seems that the hysterical woman today has a better chance of a hearing if she presents with a depressive picture, even evoking suicidal ideas.” Although hysteria today is discredited as a diagnosis, it is interesting that older clinicians such as Frei saw it as a diagnosis that trumped depression; he even argued that his patients at Cery Hospital were modeling their symptoms to conform to the new diagnoses. The 1950s and 1960s saw alternative diagnoses to the nervous syndrome come and go, fragments of clinical experience that seemed to make sense to individual physicians but were not more widely taken up because their originators did not have prestigious academic appointments. Take “the housewife syndrome” that Palma Formica proposed in 1962.
New Life and Near Death: 1912– 1914
Authors: Lorbiecki Marybeth
Published: November 2020

Estella said yes. After such news, Aldo could hardly concentrate. He wrote home, “Somehow, this time, I don’t seem to be able to write.” On December 2, he wrote in his work journal, “In at least 6 lines of work today and nothing particularly accomplished in any one.” Aldo celebrated the holidays and his engagement at the Bergeres’ with his father beside him, warmly regaled with guitar music, Spanish and Italian carols, pasta, luminarias, and piñatas. Then came the promenade of New Year’s fiestas and parties honoring New Mexico’s statehood. Work looked pretty dull in comparison. On his return to Tres Piedras, Leopold found his desk buried under requests for grazing permits. Altogether, Carson headquarters had received applications for 220,000 sheep. The new plan allowed only 198,000, and it was Leopold’s job to reject the extra applications and to make the decisions stick. He and his rangers patrolled the forests, their six-shooters at their sides. Even so, they relied mostly on forceful words as a means of persuasion. When he met ranchers or sheepers to talk, Leopold carefully left his pistols in his saddle. By March, the business of permits was well under way. Hall had accomplished the job he came for, and he moved on. Ringland promoted Leopold to acting supervisor of Carson National Forest. Aldo boasted to his fiancée: “Of all the men in our class from Forest School there are only two of us Acting Supervisors, and none are Supervisors yet.” By fall, he was Carson’s full supervisor. Leopold hired more rangers to hold the grazing situation steady. He closely inspected the rangers’ stations, work journals, and reports. When a forester’s idea or accomplishment impressed him, he dashed off “Bully!” in the margin. That summer, Aldo built a house for his bride- to- be, assisted by Estella’s brother and his own brother Frederic, who was working at headquarters for the summer. Aldo’s correspondence to his beloved never faltered.
Surveying the Field: 1924– 1933
Authors: Lorbiecki Marybeth
Published: November 2020

Since Assistant Director Leopold was not needed at the lab until July 1, he took the train with Starker and Luna to Burlington to visit his mother and brothers. (Marie had married and moved to Illinois with her husband.) Together again, the “boys” immediately began plans for a trip—this time to Carhart’s proposed wilderness area in the boundary waters of Minnesota for two weeks of canoeing, camping, and fishing. Prior to trip departure, though, Aldo had to travel to Madison to prepare the way for the family move. Starker and his uncles Carl and Frederic headed straight to Ely, Minnesota, to arrange for the canoes and equipment (Luna stayed with Opa Leopold to await the arrival of the rest of his family). Their missions accomplished, Aldo and the other adventurers met and set off into the wilds of the Superior National Forest and the Canadian Quetico. The Leopold brothers had at last reached their magical North. For two weeks, the voyageurs paddled past granite outcroppings and tall pines, fishing for trout and listening to the mournful wail of loons. Aldo wrote in his journal, “The number of adventures awaiting us in this blessed country seems with­out end.” Later he added, “How Dad would have loved it! I am reminded of Isaac [sic] Walton’s terse but loving tribute—‘an excellent angler, now with God.’” Leopold and Starker returned to Madison, an “awfully dolled up town.” He had written earlier to Estella: “Nobody has any backyard except in the slums—not even a woodshed or fence or chickens—the backyards are open lawns just as the fronts. We have a little garden room at this place I am thinking of—which is not usually the case, but nobody keeps chickens, so we would do so at our own peril!” The rest of the family arrived shortly, and the Leopolds moved into a rented home “not far from the country.” Within the month, they bought a stucco house about a mile from the lab—at 2222 Van Hise Avenue—and their energies went into transforming it into a real home.
All in the Family
Authors: Lorbiecki Marybeth
Published: November 2020

If you amble through the curving lanes of Burlington’s Aspen Grove Cemetery, designed by Aldo’s Grandfather Starker, you will come upon the Starker family vault nestled on a woody knoll. Pines and oaks guard simple stones inset in the grass marking the graves of Aldo and Estella. Aldo had returned to the land and family that had first instilled the land ethic within him. Then Clara Leopold died within a few months of her beloved eldest. Marie, Carl, and Frederic Leopold remained active in Burlington and in local conservation, with Fred becoming nationally renowned for his work with wood ducks. Thankfully for Estella, shortly after losing her husband, new grandbabies arrived on the scene, with new children for Luna and his wife Carolyn, Nina and her husband Bill, Carl and his wife Keena (Starker and Betty also had a child born that year). Though bowed by grief, Estella was made of the same strong stuff as her New Mexican ancestors, and after a few years, she slowly built back her life, now solo. Nina recalled, “Mother grew into her own person,” even traveling to Cuba and to Germany with her family. But Estella also continued to tend to the Shack land, as it tended to her. “Cultured, gentle, talented” as the Madison Free Press described “Stella”, she started to speak out publicly about local conservation issues while kindly serving as “an adopted grandmother” and mentor to graduate students and neighbors. In 1973, Northland College awarded Mrs. Estella Bergere Leopold an honorary doctorate of science. The degree was presented to her at the familiar haunts of the Wildlife Ecology Department. About two years later, in January 1975, on a visit to her family in Santa Fe, Estella grew ill and died at the age of eighty-five, a couple of days after her husband’s birthday. Her burial in Burlington next to Aldo, her sister Dolores, and twice brother-in-law, Carl, symbolized the integral intertwining of the Leopold and Luna-Otero-Bergere families.
The Shack, the Aldo Leopold Foundation, and Other Leopold Initiatives
Authors: Lorbiecki Marybeth
Published: November 2020

The framed black-and-white photograph on my wall is entitled “The Temptation of David.” It captures a young woman perched on a stump, hiking boots dangling, wet hair and flowered cotton shirt and khakis slightly damp, holding an apple with one bite missing. Standing next to her is the David in question. Behind them is the Leopold Shack, easily recognizable to any who have been there. My husband-to-be, David Mataya, and I had just snuck back to the Shack, after a quick, crazy, unguarded dip in the river. I was young, in love with David and in love with Leopold (of whom I was writing a biography for children), and completely entranced by this piece of land so lovingly restored to its natural state. I have returned numerous other times. I came the spring after Nina had died, when I was working on a religious ecology project. I was hoping, like Art Hawkins, that it would help wake up people about the Judeo-Christian call from Genesis to care for this earth and all its creatures—which God had called “good”—and to help heal this world of many ecological wounds. The project had completely stalled, and like a pilgrim, I needed to stop at the Shack. I ended up in the sand near the river, weeping. The birds in all tones and rhythms calling from tree to tree, the multitude of different trees and bushes, the flowing river, and even the small draba called forth hope. I see the draba, in its small perennial patience, has proved right. In 2014, Pope Francis issued an encyclical, or major Catholic Church teaching, not just to Catholics, but to the world, on the religious, spiritual, social, ethical, and economic reasons on why our must change its ways, just as Leopold once did, but from the perspective of faith. And he has followed this up with visits to the United States Congress and the United Nations to emphasize the need to deal immediately with climate change.
Best Synthetic Methods: Functional Group Transformations
Authors: Taber Douglass F.
Published: November 2020

Vinyl glycine 2 is a useful precursor to a variety of amino acids. Timothy E. Long of the University of Georgia found (Tetrahedron Lett. 2009, 50, 5067) that the o-nitrophenyl sulfoxide 1 eliminated smoothly in refluxing toluene. Alicia Boto and Rosendo Hernández of IPNA La Laguna observed (Tetrahedron Lett. 2009, 50, 3974) that a related selenoxide elimination proceeded to give the single regioisomer 4. Avelino Corma of the Universidad Politécnica de Valencia developed ( Chemical Commun. 2009, 4947) a gold catalyst for the selective hydroboration of alkynes over alkenes. Eiji Shirakawa and Tamio Hayashi of Kyoto University devised (Chemical Commun. 2009, 5088) a Ru catalyst for the conversion of an alkenyl triflate such as 8 to the corresponding bromide. Tristan H. Lambert of Columbia University found (J. Am. Chem. Soc. 2009, 131, 13930) that the dichloride 11 smoothly converted a variety of alcohols into the corresponding chlorides. Crown ethers have been used to promote SN2 reactivity by solubilizing the metal cation. Sungyul Lee of Kyunghee University, Dae Yoon Chi of Sogang University, and Choong Eui Song of Sungkyunkwan University demonstrated (Angew. Chem. Int. Ed. 2009, 48, 7683) that the inexpensive polyethylene glycols were also effective. Mugio Nishizawa of Tokushima Bunri University devised (Synlett 2009, 1175) conditions for the rapid regioselective hydration of hydroxy alkynes such as 15. Jaume Vilarrasa of the Universitat de Barcelona developed (Organic Lett. 2009, 11, 4414) a mild alternative protocol for the Nef reaction, converting a nitroalkane such as 17 into the corresponding ketone under neutral conditions. Clément Mazet of the University of Geneva optimized (Tetrahedron Lett. 2009, 50, 4141) the Ir-catalyzed conversion of an allylic alcohol 19 into the saturated aldehyde. Jonathan M. J. Williams of the University of Bath established (Angew. Chem. Int. Ed. 2009, 48, 7375) that under Ir-catalyzed “borrowing hydrogen” conditions, alkyl amines could donate alkyl groups to anilines such as 21. Danfeng Huang and Yulai Hu of Northwest Normal University devised (Organic Lett. 2009, 11, 4474) a simple protocol for conversion of an acid 23 to the Weinreb amide 24. of the Universitat
Best Synthetic Methods: Oxidation
Authors: Taber Douglass F.
Published: November 2020

Karl A. Scheidt of Northwestern University described (Organic Lett. 2009, 11, 1651) the oxidation of primary alcohols such as 1 in the presence of an indole 2. The product 3, an active acylating agent, is readily converted to other esters and amides. K. Rajender Reddy of the Indian Institute of Chemical Technology, Hyderabad, developed (Tetrahedron Lett. 2009, 50, 2050) a protocol for the direct oxidation of a primary amine 4 to the corresponding nitrile 5. In the presence of ammonia, the same procedure converted aldehydes and primary alcohols into the nitriles. Several catalytic methods for the oxidation of alcohols to aldehydes and ketones have recently been put forward. René Grée of the Université de Rennes 1 found ( Tetrahedron Lett. 2009, 50, 1493) that ZnBr2 catalyzed the oxidation of alcohols with diethyl azodicarboxylate. Tsutomu Katsuki of Kyushu University designed (Tetrahedron Lett. 2009, 50, 3432) a Ru catalyst for the air oxidation of primary alcohols to aldehydes. Kazuaki Ishihara of Nagoya University showed (J. Am. Chem. Soc. 2009, 131, 251) that 1 mol % of 10 was sufficient to catalyze the oxidation of 6 to 7. With excess oxidant, 7 was carried on cleanly to 11. Nitroxyl radicals such as TEMPO have long been used to catalyze oxidations. Yoshiharu Iwabuchi of Tohoku University developed (J. Org. Chem. 2009, 74, 4619) a simple preparation of 13 , the most efficient such catalyst reported so far. This catalyst should also be useful for the oxidation reported by Professor Iwabuchi (Chem. Commun. 2009, 1739) of primary alcohols and aldehydes to the corresponding carboxylic acids. David S. Forbes of the University of South Alabama prepared (Tetrahedron Lett. 2009, 50, 1855) 16 by combining thioanisole with N-bromosuccinimide. The reagent 16 efficiently sulfenylated active methylene compounds. Jiri Srogl of the Academy of Sciences of the Czech Republic established (Organic Lett. 2009, 11, 843) conditions for the oxidation of primary and secondary amines to aldehydes and ketones. Olga A. Ivanova of Moscow State University demonstrated (Tetrahedron Lett. 2009, 50, 2793) that DMDO 21 could oxidize a sensitive amino cyclopropane such as 20 to the corresponding nitro compound.
New Methods for Carbon-Carbon Bond Construction
Authors: Taber Douglass F.
Published: November 2020

Sunggak Kim of KAIST reported (Synlett 2009, 81) an improved protocol for the one-carbon free radical homologation of an iodide such as 1 to the nitrile. Primary, secondary, and tertiary iodides work well. We described (Tetrahedron Lett. 2009, 50, 2462) a procedure for the one-carbon homologation of a halide 4 directly to the benzyl ether 6. Bin Xu of Shanghai University showed (Chem. Commun. 2009, 3246) that conversion of a ketone 8 to the 1,1-dibromoalkene set the stage for the net one-carbon homologation to the amide 9. A. Fernández-Mateos of the Universidad de Salamanca uncovered (J. Org. Chem. 2009, 74, 3913) a powerful new branching reaction, condensing the more substituted center of an epoxide 10 with a nitrile 11 to deliver the adduct 12. Useful diastereocontrol was observed with cyclic epoxides. Uli Kazmaier of the Universität des Saarlandes optimized (Adv. Synthy. Cat. 2009, 351, 1395) a Mo catalyst for the hydrostannation of a terminal alkene 13 to the branched product 14. Dong-Mei Cui of the Zhejiang University of Technology and Chen Zhang of Zhejiang University (both in Hangzhou) developed (Chem. Commun. 2009, 1577) a complementary procedure, converting the terminal alkene 15 into the branched alkenyl tosylate 16. The Wittig reaction is notorious for racemizing sensitive aldehydes. Hélène Lebel of the Université de Montréal demonstrated (Organic Lett. 2009, 11, 41) a simple one-pot protocol for sequential oxidation and homologation of 17 that preserved the integrity of the adjacent stereogenic center. The stereocontrolled construction of trisubstituted alkenes is still a major issue in organic synthesis. Giancarlo Verardo of the University of Udine established (J. Phys. Org. Chem. 2009, 22, 24) that the α-diazo ester 19, readily prepared directly from the simple ester, was converted by I2 to the alkene 20 with high geometric control. Condensation with the Ohira reagent 22 is often the method of choice for converting an aldehyde into the homologated alkyne. Hubert Maehr and Milan Uskokovic of Bioxell and Carl P. Schaffner of the Waksman Institute described (Syn. Commun. 2009, 39, 299) an optimized, scalable procedure for the in situ preparation of 22 and the conversion of 21 to 23. Note, again, that the sensitive stereogenic center adjacent to the intermediate aldehyde was not epimerized under the reaction conditions.
New Methods for C-C Bond Construction
Authors: Taber Douglass F.
Published: November 2020

Luigino Troisi of the University of Salento found (Tetrahedron Lett. 2010, 51, 371) that a variety of primary and secondary amines could be coupled with a benzylic halide 1 under carbonylating conditions. Ilhyong Ryu of Osaka Prefecture University showed (Organic Lett. 2010, 12, 1548) that under reducing conditions, an iodide 3 coupled with CO to give the primary alcohol. Felicia A. Etzkorn of Virginia Tech observed (Organic Lett. 2010, 12, 696) that under Hg hydrolysis conditions, the orthothioester derived from 5 coupled with 6 to give 7. Yasuharu Yoshimi of the University of Fukui and Minoru Hatanaka of Iwate Medical University devised (Tetrahedron Lett. 2010, 51, 2332) conditions for the decarboxylative addition of the acid 8 to 9 to give 10. Yong-Min Liang and Xiaojun Yao of Lanzhou University and Chao-Jun Li of McGill University described (J. Org. Chem. 2010, 75, 783) a related procedure with α-amino acids. Yasutaka Ishii of Kansai University established (J. Am. Chem. Soc. 2010, 132, 2536) that t -butyl acetate 12 was an effective partner for the Ir-mediated oxidation-coupling-reduction of an alcohol 11. He used (J. Org. Chem. 2010, 75, 1803) a similar protocol to condense acetone with the diol 14, to give the long-chain diketone 16. The formation of allylic Grignard reagents can be inefficient because the excess reactive halide tends to couple with the Grignard reagent as it forms. Brandon L. Ashfeld of the University of Notre Dame found (Tetrahedron Lett. 2010, 51, 2427) a simple solution to this problem: inclusion of a catalytic amount of the inexpensive Cp2 TiCl2 to mediate the addition of 18 to 17. Brian T. Connell of Texas A&M University demonstrated (J. Am. Chem. Soc. 2010, 132, 7826) that with Mn, 21 could be added to 20. The acetate 21 is thus an easily prepared homoenolate equivalent. Note that although 21 is an E/Z mixture, the product 22 is cleanly Z. Gérard Cahiez of the Université de Paris 13 reported (Synlett 2010, 299) a detailed study of the Cu-catalyzed coupling of 24 with 23. Without supporting ligands, slow addition (syringe pump, 1 h) of 24 to 23 assured clean formation of 25. Manual slow addition (dropping funnel, 15 min) was not effective.
Functionalization and Homologation of Alkenes
Authors: Taber Douglass F.
Published: November 2020

Masahito Ochiai developed (Org. Highlights, March 24, 2008) the iodosobenzene-mediated cleavage of alkenes to keto aldehydes. Thottumkara K. Vinod of Western Illinois University described (Org. Lett. 2010, 12, 5640) a modified protocol that delivered the keto acid 2. Chi-Ming Che of the University of Hong Kong established (J. Am. Chem. Soc. 2010, 132, 13229) a method for the preparative scale Fe-catalyzed cis dihydroxylation of an alkene 3. Ilhyong Ryu of Osaka Prefecture University devised (Synlett 2010, 2014) a practical procedure for the free radical addition of HBr to an alkene 5. Tetsuo Ohta of Doshisha University showed (Tetrahedron Lett. 2010, 51, 2806) that a Ru catalyst could add an aromatic acid to the internal carbon of a terminal alkene 7. Noriki Kutsumura and Takao Saito of the Tokyo University of Science found (Org. Lett. 2010, 12, 3316) conditions for bromination/dehydrobromination to convert 10 to 11. Tsuyoshi Taniguchi of Kanazawa University oxidized (J. Org. Chem. 2010, 75, 8126) the alkene 12 to the nitro alkene 13. Professor Taniguchi added (Angew. Chem. Int. Ed. 2010, 49, 10154) methyl carbazate to 14 to give the β-hydroxy ester 15. Philippe Renaud of the University of Bern effected (J. Am. Chem. Soc. 2010, 132, 17511) the free radical homologation of 16 to the azide 18. Daniel P. Becker of Loyola University described (Tetrahedron Lett. 2010, 51, 3514) the elegant diastereoselective Pd-catalyzed bis-methoxycarbonylation of 19 to the diester 20. Matthew S. Sigman of the University of Utah established (J. Am. Chem. Soc. 2010, 132, 13981) the oxidative Heck arylation of 21 to 23. F. Dean Toste of the University of California, Berkeley, found (Org. Lett. 2010, 12, 4728) that the intermediate in the gold-catalyzed alkoxylation of 24 could couple to an aryl silane 25 to give 26. Chun-Yu Ho of the Chinese University of Hong Kong used (Angew. Chem. Int. Ed. 2010, 49, 9182) a Ni catalyst to add styrene 27 to the alkene 24. Masahiro Miura of Osaka University effected (J. Org. Chem. 2010, 75, 5421) the oxidative coupling of 29 with styrene 27 to give the linear product 30.
Progress in Alkene and Alkyne Metathesis: (+)-5- epi -Citreoviral(Funk) and ( ± )-Poitediol (Vanderwal)
Authors: Taber Douglass F.
Published: November 2020

The Fischer carbene 2 at 0.5 mol % gives only 12% conversion of 1 to 4 after 18 hours. Debra J. Wallace of Merck Process showed (Adv. Synth. Cat. 2009, 351, 2277) that addition of a catalytic amount of the inexpensive 3 activated 2 , leading to 95% conversion of 1 to 4 after 18 hours. Shazia Zaman of the University of Canterbury and Andrew D. Abell of the University of Adelaide found (Tetrahedron Lett. 2009, 50, 5340) that the catalyst 5, incorporating a polyethylene glycol (PEG) chain, was readily recovered in active form by precipitation and could be reused at least fi ve times. Zhu Yinghuai of the Institute of Chemical and Engineering Sciences, Singapore (Adv. Synth. Cat. 2009, 351, 2650), and Chao Che, Zhen Yang, and Biwang Jiang of Peking University (Chem. Commun. 2009, 5990) independently described the preparation of Ru complexes such as 5 bound to magnetic nanoparticles. The catalysts were easily recycled and reused, leaving < 4 ppm Ru in the product. Reto Dorta of the University of Zurich reported (J. Am. Chem. Soc. 2009, 131, 9498) that the complex 6 (Ar = 2,7-diisopropylnaphthyl) was a separable mixture of syn- and anti-isomers. The very reactive anti-isomer at 50 ppm converted neat 1 into 2 in 2 hours at room temperature. Richard R. Schrock of MIT devised (J. Am. Chem. Soc. 2009, 131, 10840) an efficient Mo catalyst for a long-sought transformation—the ethenolysis of long-chain alkenes such as 7. Robert A. Stockman of the University of Nottingham developed (Chem. Commun. 2009, 4399) a related Ru-catalyzed procedure: cross-metathesis ring opening with methyl acrylate 11. Amir A. Hoveyda of Boston College, a coauthor on the Schrock paper, used (J. Am. Chem. Soc. 2009, 131, 10652) a very similar Mo catalyst for the rapid cross-metathesis of an alkyne with ethene, leading after subsequent ring-closing metathesis to products such as 14. Alois Fürstner of the Max-Planck-Institut, Mülheim, described (J. Am. Chem. Soc. 2009, 131, 9468) a well-characterized Mo nitride complex that efficiently catalyzed the conversion of 15 into 16. Samir Bouzbouz of the Université de Rouen and Janine Cossy of ESPCI ParisTech established (Organic Lett. 2009, 11, 5446) conditions for the metathesis of alkenes with the linchpin 18.
Alkene and Alkyne Metathesis: Grandisol (Goess), 8-Epihalosilane (Kouklovsky/Vincent), (+)-Chinensiolide B (Hall)
Authors: Taber Douglass F.
Published: November 2020

The cost of using Grubbs-type catalysts could be reduced dramatically if the turnover could be improved. Richard L. Pederson of Materia found (Organic Lett. 2010, 12, 984) that in MTBE at 50°C, the ring-closing metathesis of 1 proceeded to completion in 8 hours with just 500 ppm of H2 catalyst 2. Jianhui Wang of Tianjin University constructed (Angew. Chem. Int. Ed. 2010, 49, 4425) a modified H2 catalyst 5 tethered to a nitrobenzospiropyran. After the cyclization of 4 to 6 was run in CH2Cl2, the mixture was irradiated with visible light, converting 5 into its ionic form, which could be extracted with glycol/methanol, leaving little Ru residue in the cyclized product. In the dark, the catalyst reverted and could be extracted back into CH2Cl2 and reused. In a complementary approach, David W. Knight of Cardiff University found (Tetrahedron Lett. 2010, 51, 638) that the residual Ru after metathesis could be reduced to < 2 ppm simply by stirring the product with H2O2. Cyclopropenes such as 6 are readily available in enantiomerically pure form by the addition of diazoacetates to alkynes. Christophe Meyer and Janine Cossy of ESPCI ParisTech showed (Organic Lett. 2010, 12, 248) that with a Ti additive, G2 cyclized 7 to 8. Siegfried Blechert of the Technische Universität Berlin devised (Angew. Chem. Int. Ed. 2010, 49, 3972) the chiral Ru catalyst 11, which converted the prochiral 9 to 12 in high ee. Daesung Lee of the University of Illinois, Chicago, explored (J. Am. Chem. Soc. 2010, 132, 8840) the cyclization of the diyne 13 with 14 under G2 catalysis. Depending on the terminal substituent, the cyclization could be directed selectively to 15 or 16. Bran C. Goess of Furman University took advantage (J. Org. Chem. 2010, 75, 226) of alkyne ring-closing metathesis for the conversion of 17 to 18. Selective hydrogenation then delivered the boll weevil pheromone grandisol 19. Cyrille Kouklovsky and Guillaume Vincent of the Université de Paris Sud extended (J. Org. Chem. 2010, 75, 4333) ring-opening/ring-closing metathesis to the nitroso Diels-Alder adduct 20. Reduction led to 8-epihalosilane 22.
Enantioselective Preparation of Alcohols and Amines: The Lam Synthesis of (+)-Tanikolide
Authors: Taber Douglass F.
Published: November 2020

Takashi Ooi of Nagoya University effected (J. Am. Chem. Soc. 2010, 132, 12240) the enantioselective protonation of ketene silyl acetals such as 1 to give 2 in high ee. Hyeon-Kyu Lee of the Korean Research Institute of Chemical Technology achieved (Org. Lett. 2010, 12, 4184) high ee in the hydrogenation of the cyclic sulfamidate 3 to 4. Doo Ok Jang of Yonsei University combined (J. Am. Chem. Soc. 2010, 132, 12168) the nucleophilic allyl indium with a protonated chiral amine to effect homologation of 5 to 6. Ryo Shintani and Tamio Hayashi of Kyoto University reported (Org. Lett. 2010, 12, 4106) a related advance with tetraarylborates. Kazuaki Ishihara, also of Nagoya University (Org. Lett. 2010, 12, 3502) and Yoshihiro Sohtome and Kazuo Nagasawa of the Tokyo University of Agriculture and Technology (Angew. Chem. Int. Ed. 2010, 49, 9254) devised conditions for adding malonate to imines such as 7. Professors Shintani and Hayashi also employed (J. Am. Chem. Soc. 2010, 132, 13168) tetraarylborates to convert 9 to the α-quaternary amine 10. Professor Ooi (Angew. Chem. Int. Ed. 2010, 49, 5567) and Wanbin Zhang of Shanghai Jiao Tong University (J. Am. Chem. Soc. 2010, 132, 15939) prepared α-quaternary amino acids such as 12 by nucleophilic rearrangement of 11. Keiji Maruoka, also of Kyoto University, reported (J. Am. Chem. Soc. 2010, 132, 17074; not illustrated) a catalytic enantioselective conjugate addition approach to α-quaternary amines. Shuji Akai of the University of Shizuoka converted (Org. Lett. 2010, 12, 4900) the racemic allylic alcohol 13 to the enantiomerically enriched acetate 14 by combining V-catalyzed equilibration with lipase-catalyzed acylation. Toshiro Harada of the Kyoto Institute of Technology added (Org. Lett. 2010, 12, 5270) the alkenylboron 16 to the aldehyde 15 with high ee. Xiang Zhou of Wuhan University and Lin Pu of the University of Virginia significantly improved (Tetrahedron Lett . 2010, 51, 5024) a protocol for the enantioselective addition of aliphatic alkynes to aliphatic aldehydes. For other enantioselective additions to aldehydes (not illustrated), see J. Org. Chem. 2010, 75 , 5326 and Org. Lett. 2010, 12, 5088.