OpenLLM-France/wikimedia huggingface dataset:
# Bertinotti (surname)

Bertinotti is an Italian surname. Notable people with the surname include:
* Dominique Bertinotti (born 1954), French politician
* Fausto Bertinotti (born 1940), Italian politician
* Teresa Bertinotti, also known as Teresa Bertinotti-Radicati (1776–1854), Italian soprano and voice teacher
# Aviation Drug-Trafficking Control Act of 1984

Aviation Drug-Trafficking Control Act of 1984 is a United States Federal law amending the Federal Aviation Act of 1958. The statutory law authorized criminal penalties for the unlawful aerial transportation of controlled substances. The Act of Congress mandated the revocation of aircraft registrations and airman certificates by the Federal Aviation Administration whereas an aircraft aviator knowingly engages in the transit of illicitly used drugs. The Act established authority and a statute of limitations for the reissuance of airman certificates by the United States Secretary of Transportation.
The S. 1146 legislation was passed by the 98th U.S. Congressional session and enacted into law by the 40th President of the United States Ronald Reagan on October 19, 1984.

## History

In 1982, the United States created the Operation Bahamas, American, Turks and Caicos (OPBAT) initiative harmonizing an interdiction for the narcotic drug trafficking in the West Indies waters. The Bahamas and Turks and Caicos initiative was a cooperative drug interdiction operation supported by an alliance of federal enforcement organizations as coordinated by;
* ☆ Drug Enforcement Administration
* ☆ Law Enforcement Detachments
* ☆ Royal Bahamas Police Force
* ☆ Royal Turks and Caicos Islands Police Force
* ☆ United States Atlantic Command
* ☆ United States Coast Guard
* ☆ United States Coast Guard Tactical Squadron
* ☆ United States Customs and Border Protection
* ☆ United States Southern Command

### Federal Anti-Crime Task Force for Southern Florida

In January 1982, the Reagan Administration established the Federal Anti-Crime Task Force for Southern Florida standardizing a multi-jurisdictional law enforcement organization for confronting organized crime in the Caribbean, Gulf of Mexico, and Southeastern United States. The Florida Counter-drug Task Force developed and governed containment measures for the domestic and international enterprises sustaining illegal drug trade activities in the Lucayan Archipelago and Straits of Florida.
In October 1982, United States President Ronald Reagan made a public announcement from the Great Hall of the Robert F. Kennedy Department of Justice Building. The presidential public declaration addressed the federal initiatives related to the interdiction of drug trafficking and organized crime confronting the United States borders and continental maritime boundaries.

### National Narcotics Border Interdiction System

In March 1983, the Reagan Administration announced the formation of the National Narcotics Border Interdiction System (NNBIS). The National Narcotics Border Interdiction established an air, land, and sea anti-smuggling engagement while supporting the federal controlled substance enforcement operations of the South Florida Task Force.
# Breda Ba.33

The Breda Ba.33 was an Italian light sport aircraft designed and built by the Breda company.

## Design and development

Ing Cesare Pallavicino of the Breda company led the design and development of the Ba.33. The first version, the Ba.33 Serie 1, was a two-seat low-wing monoplane with external bracing between the wings and the fuselage. It was powered by an 89-kilowatt (120-horsepower) de Havilland Gipsy III four-cylinder air-cooled inline engine. Later, two versions of the Ba.33 Serie 2 appeared, one with the de Havilland Gipsy engine and another with a Colombo engine.
Breda also developed a single-seat version of the aircraft, the Ba.33S; differing from the Ba.33 in being a single-seater and having an enclosed cockpit and a more powerful engine, the 97 kW (130.08 hp) Colombo S63 engine.

## Operational history

After the Ba.33 first flew in 1930, the aircraft and its variants proved to be a very successful series of touring and racing aircraft during the 1930s. In 1931, a Ba.33 won the Giro aereo d'Italia ("Air Tour of Italy") race.
Ba.33s were the equipment of the Italian team for the International Touring Competition in 1932, with which also Winifred Spooner entered the contest. Ambrogio Colombo was a leader in the contest after technical trials. However, two Bredas crashed on 23 August 1932, due to weak wing construction (one mechanic died bailing out), and Italy decided to withdraw all the Italian teams from the contest.

## Variants
### Ba.33 Serie 1

    Original two-seat version with 89-kilowatt (120-horsepower) de Havilland Gipsy III engine.

### Ba.33 Serie 2

    Two versions, one offered with a de Havilland Gipsy engine and one with a 130 hp (97 kW) Colombo S.63 engine.

### Ba.33S

    Improved single-seat version with enclosed cockpit and 140 hp (104 kW) Colombo S.63 engine.

## Operators

Japan
* Mainichi Shimbun a Japanese newspaper.

## Specifications (Ba.33 Serie 1)

Data from Italian Civil and Military aircraft 1930-1945
General characteristics
* Crew: 2
* Length: 6.78 m (22 ft 3 in)
* Wingspan: 9.40 m (30 ft 10 in)
* Wing area: 15.00 m$^2$ (161.5 sq ft)
* Empty weight: 429 kg (946 lb)
* Gross weight: 828 kg (1,826 lb)
* Powerplant: 1 × de Havilland Gipsy III 4-cyl. inverted in-line, air-cooled piston engine, 89 kW (120 hp)
* Powerplant: 1 × Colombo S.63 6-cyl. air-cooled in-line piston engine,, 100 kW (140 hp) (Serie 2 and Ba.33S)
Performance
* Maximum speed: 230 km/h (143 mph, 124 kn)
* Cruise speed: 200 km/h (124 mph, 108 kn)
* Stall speed: 85 km/h (53 mph, 46 kn)
* Range: 1,800 km (1,120 mi, 970 nmi)
* Service ceiling: 7,000 m (22,960 ft)
* Rate of climb: 4.44 m/s (874 ft/min)
* Time to altitude: 13,120 ft (3,998.98 m) in 15 minutes
# Biathlon World Championships 2016 – Men's mass start

The Men's mass start event of the Biathlon World Championships 2016 was held on 13 March 2016. 30 athletes will participate over a course of 15 km.

## Results

The race was started at 16:00 CET.
| Rank | Bib | Name | Nationality | Time | Penalties (P+S+P+S) | Deficit |
| | 8 | Johannes Thingnes Bø | Norway | 37:05.1 | 1 (0+0+1+0) | |
| | 1 | Martin Fourcade | France | 37:07.9 | 1 (1+0+0+0) | +2.8 |
| | 2 | Ole Einar Bjørndalen | Norway | 37:11.8 | 0 (0+0+0+0) | +6.7 |
| 4 | 21 | Dominik Windisch | Italy | 37:24.9 | 2 (1+0+0+1) | +19.8 |
| 5 | 14 | Arnd Peiffer | Germany | 37:25.0 | 1 (1+0+0+0) | +19.9 |
| 6 | 9 | Tarjei Bø | Norway | 37:26.9 | 2 (1+1+0+0) | +21.8 |
| 7 | 16 | Jakov Fak | Slovenia | 37:27.0 | 1 (0+0+1+0) | +21.9 |
| 8 | 4 | Serhiy Semenov | Ukraine | 37:36.7 | 0 (0+0+0+0) | +31.6 |
| 9 | 7 | Anton Shipulin | Russia | 37:46.1 | 2 (0+1+0+1) | +41.0 |
| 10 | 27 | Lowell Bailey | United States | 37:46.8 | 1 (0+0+0+1) | +41.7 |
| 11 | 6 | Simon Eder | Austria | 37:58.2 | 2 (0+0+0+2) | +53.1 |
| 12 | 24 | Tim Burke | United States | 37:58.5 | 2 (0+0+1+1) | + 53.4 |
| 13 | 26 | Vladimir Chepelin | Belarus | 38:01.2 | 2 (0+1+1+0) | +56.1 |
| 14 | 15 | Erik Lesser | Germany | 38:07.9 | 2 (0+0+0+2) | +1:02.8 |
| 15 | 3 | Dominik Landertinger | Austria | 38:10.3 | 3 (2+1+0+0) | +1:05.2 |
| 16 | 28 | Anton Babikov | Russia | 38:11.4 | 2 (1+0+0+1) | +1:06.3 |
| 17 | 19 | Michal Šlesingr | Czech Republic | 38:13.2 | 3 (1+0+1+1) | +1:08.1 |
| 18 | 13 | Benedikt Doll | Germany | 38:14.3 | 3 (0+0+1+2) | +1:09.2 |
| 19 | 10 | Simon Schempp | Germany | 38:19.3 | 3 (0+0+1+2) | +1:14.2 |
| 20 | 12 | Quentin Fillon Maillet | France | 38:26.8 | 3 (1+0+1+1) | +1:21.7 |
| 21 | 20 | Vladimir Iliev | Bulgaria | 38:39.4 | 3 (0+0+1+2) | +1:34.3 |
| 22 | 18 | Michal Krčmář | Czech Republic | 38:42.1 | 2 (0+0+1+1) | +1:37.0 |
| 23 | 11 | Evgeniy Garanichev | Russia | 38:42.5 | 4 (2+1+0+1) | +1:37.4 |
| 24 | 17 | Simon Desthieux | France | 39:08.7 | 3 (0+0+2+1) | +2:03.6 |
| 25 | 25 | Krasimir Anev | Bulgaria | 39:18.2 | 3 (0+0+1+2) | +2:13.1 |
| 26 | 30 | Andrejs Rastorgujevs | Latvia | 39:30.7 | 3 (1+1+1+0) | +2:25.6 |
| 27 | 23 | Serafin Wiestner | Switzerland | 40:01.3 | 4 (2+0+1+1) | +2:56.2 |
| 28 | 5 | Emil Hegle Svendsen | Norway | 40:42.7 | 4 (1+0+0+3) | +3:37.6 |
| 29 | 22 | Yan Savitskiy | Kazakhstan | 41:17.8 | 6 (0+2+2+2) | +4:12.7 |
| — | 29 | Leif Nordgren | United States | DNF | DNF | DNF |
# 1923 William & Mary Indians football team

The 1923 William & Mary Indians football team represented the College of William & Mary as an independent during the 1923 college football season. Led by first-year head coach J. Wilder Tasker, the Indians compiled a record of 6–3.

## Schedule

| Date | Opponent | Site | Result | Attendance |
| September 29 | at Navy | Worden FieldAnnapolis, MD | L 10–39 | |
| October 6 | at Syracuse | Archbold StadiumSyracuse, NY | L 3–63 | 10,000 |
| October 13 | Guilford | Williamsburg, VA | W 74–0 | |
| October 20 | vs. Trinity (NC) | Rocky Mount, NC | W 21–0 | |
| October 27 | Randolph–Macon | Williamsburg, VA | W 27–0 | |
| November 3 | vs. Hampden–Sydney | Norfolk, VA | W 20–0 | |
| November 10 | Delaware | Williamsburg, VA (rivalry) | W 14–0 | |
| November 17 | at Roanoke | Roanoke Fair GroundsRoanoke, VA | L 7–9 | |
| November 29 | at Richmond | Stadium FieldRichmond, VA (rivalry) | W 27–6 | |
# Athletics at the 2007 Pan American Games – Men's hammer throw

The men's hammer throw event at the 2007 Pan American Games was held on July 25.

## Results

| Rank | Athlete | Nationality | #1 | #2 | #3 | #4 | #5 | #6 | Result | Notes |
| | James Steacy | Canada | 71.60 | 73.77 | 71.14 | x | 73.52 | 71.31 | 73.77 | |
| | Kibwe Johnson | United States | x | 69.08 | x | 70.72 | 68.93 | 73.23 | 73.23 | |
| | Juan Ignacio Cerra | Argentina | 70.61 | 71.57 | 68.24 | 69.92 | 70.89 | 72.12 | 72.12 | |
| 4 | A. G. Kruger | United States | 66.31 | 65.82 | 68.48 | 68.71 | 66.74 | 67.40 | 68.71 | |
| 5 | Patricio Palma | Chile | 65.60 | 67.86 | 66.07 | x | 67.80 | 66.82 | 67.86 | PB |
| 6 | Noleysi Bicet | Cuba | 67.51 | 66.61 | 66.98 | x | 67.40 | 66.44 | 67.51 | |
| 7 | Wagner Domingos | Brazil | 62.50 | 63.38 | 64.11 | 62.18 | 64.03 | 65.27 | 65.27 | |
| 8 | Aldo Bello | Venezuela | 61.78 | 63.98 | 63.25 | 63.53 | x | 62.33 | 63.98 | |
| 9 | Marcos dos Santos | Brazil | 61.86 | x | 61.58 | | | | 61.86 | |
| 10 | Leonardo Pino | Chile | 60.75 | 61.61 | 61.47 | | | | 61.61 | |
| 11 | Rául Rivera | Guatemala | 60.10 | x | 57.66 | | | | 60.10 | |
| 12 | Roberto Sawyers | Costa Rica | x | x | 57.45 | | | | 57.45 | |
| 13 | Michael Letterlough | Cayman Islands | x | 55.30 | x | | | | 55.30 | |
# Blennidus poeciloides

Blennidus poeciloides is a species of ground beetle in the subfamily Pterostichinae. It was described by Straneo in 1953.
# Bach Dancing & Dynamite Society

The Bach Dancing & Dynamite Society is an oceanfront non-profit music venue located at the Douglas Beach House in Half Moon Bay, California.
The venue was founded in 1964 by Pete Douglas and is now run by his daughter, Barbara Douglas Riching.
Pete Douglas moved to Half Moon Bay in 1957. He purchased a beer joint and ran it as the Ebb Tide Cafe.
The society's name came from an informal party hosted at the Ebb Tide Cafe in 1963. While Pete and his guests danced to a Bach Brandenberg Concerti, others lit dynamite nearby on the beach. A guest suggested they call themselves the Bach Dancing & Dynamite Society and they incorporated under that name soon afterwards.
Today a member-supported non-profit, the Bach has hosted performances for more than fifty years, often featuring jazz musicians visiting the San Francisco Bay Area on larger tours.
Musicians who have performed at the Bach include Duke Ellington, Dexter Gordon, Stan Getz, Dizzy Gillespie, Count Basie and Etta James.
The Bach is listed in the DownBeat 2024 International Jazz Venue Guide as presenting "world-class jazz in an intimate setting with stunning views of the ocean."
* Arnett Cobb, 1979
* Barry Harris, 1981
* Dannie Richmond, 1981
* Red Rodney, 1982
* Phil Woods, 1983
* Emily Remler, 1984
* Tony Williams, 1986
* John Handy, 1987
* Milt Hinton, 1987
* Milt Jackson, 1980s
* Regina Carter, 2020
* Bria Skonberg, 2021
# Axel Gedaschko

Axel Gedaschko (born 1959) is a German politician, representative of the German Christian Democratic Union.
Gedaschko was born 1959 in Hamburg and is father of two children. He studied law at the University of Hamburg and Göttingen.
Since 2008 Gedaschko is state minister of Economic Affairs and Employment in Hamburg.
# Brendel

Brendel is a surname. Notable people with the surname include:
* Albert Brendel, various people
* Alfred Brendel (born 1931), pianist
* Brian Brendell (born 1986), Namibian footballer
* El Brendel (1890–1964), American entertainer
* Daniela Brendel (born 1973), German swimmer
* Franz Brendel (1811–1868), 19th-century music critic and publisher
* Franz Brendel (canoeist), German canoeist
* Günther Brendel (born 1930), German painter
* Henry W. Brendel (1857–1940), American lawyer and government official
* Jake Brendel (born 1992), American football player
* Jakob Brendel (1907–1964), German wrestler
* Joachim Brendel (1921–1974), German Luftwaffe pilot
* Karl Brendel (1871–1925), German sculptor
* Leif Brendel (1903–1972), Norwegian editor
* Maria Weigert Brendel (1902–1994), German classical art expert, wife of Otto Brendel
* Martin Brendel (1862–1939), German astronomer
* Neal Brendel (1954–2021), American rugby union player and lawyer
* Otto Brendel (1901–1973), scholar of Etruscan art
* Pascal Brendel (born 2003), German gymnast
* Robert Brendel (c. 1821–1898), German botanist and model maker
* Sarah Brendel (born 1976), German pop singer
* Sebastian Brendel (born 1988), German canoeist
* Willi Brendel (1938–2006), German field hockey player
* Wolfgang Brendel (born 1947), German opera singer
# 2019 in Danish music

The following is a list of notable events and releases of the year 2019 in Danish music.

## Events
### May

* 29 – The 21st Distortion festival starts in Copenhagen (May 29 - June 2).

### June

* 6 – The NorthSide Festival opens in Aarhus (June 6 - 8).
* 29 – The 48th Roskilde Festival opens (June 29 - July 5).

### July

* 5 – The 41st Copenhagen Jazz Festival start in Copenhagen, Denmark (July 5 – 14).
* 13 – The 31st Aarhus Jazz Festival starts in Aarhus, Denmark (July 13 – 20).
# Atlas Eclipticalis

Atlas Eclipticalis may refer to:
* Atlas eclipticalis, 1950.0 a 1958 atlas of stars by Antonín Bečvář
* Atlas Eclipticalis, a 1961–1962 composition by John Cage
# Bernard Magrez

Bernard Magrez (born 1936) is a French wine magnate who predominantly owns Bordeaux wine estates, including Château La Tour Carnet, Château Pape Clément, Château Fombrauge and Clos Haut-Peyraguey but also a large number of wine producing properties in other French wine regions and other countries, including Spain, Portugal, Chile, Argentina, Japan, Morocco and California. In 2017 it was confirmed that Magrez had bought Château Le Sartre in Bordeaux's Pessac-Léognan.

## Biography

A multi-millionaire, Magrez made his fortune as the founder of the William Pitters spirits company and the low-cost red Bordeaux brand Malesan and Sidi Brahim.
In December 2008 it was reported that the investment bank Lazard was offering Château Latour for sale, and Magrez was suggested as the likely buyer. In the July 2009 Decanter publication of "The Power List" ranking of the wine industry's individuals of influence, Magrez placed at number 29.
In 2012 expanded his Bordeaux holdings with Château Malleprat in Pessac-Léognan, Château Moulin d'Ulysse in Listrac-Médoc, and Clos Haut-Peyraguey, a classified growth in Sauternes.
Bernard Magrez is the sole owner of four classified growth chateaux located in the different prestigious Bordeaux Classified Appellations: Chateau Pape Clement in Graves, Chateau La Tour Carnet in Haut-Médoc, Chateau Fombrauge in St Emilion and Clos Haut-Peyraguey in Sauternes.
# Blennidus sanchezi

Blennidus sanchezi is a species of ground beetle in the subfamily Pterostichinae. It was described by Moret in 2005.
# Bagisara praecelsa

Bagisara praecelsa is a moth of the family Noctuidae first described by Alexander Douglas Campbell Ferguson in 1997. It is found in southern North America from Texas and northern Mexico.
The wingspan is about 30 mm.
# Best of Live

Best of Live may refer to:
* Best of Live (Bajaga i Instruktori album), 2002
* Best of Live (Johnny Clegg album), 2003
* Best of Live (Last Exit album), 1990
* Best of Live (1996–2005), an album by Kraljevski Apartman, 2005
* Best of Night Ranger Live, an album by Night Ranger, 2005
# Axel Gotthard

Axel Gotthard (born 21 April 1959) is a German historian of modern age and university teacher.
Gotthard was born in Schwäbisch Gmünd. He studied at the University of Würzburg and the University of Tübingen. He works at the University of Erlangen-Nuremberg as university teacher.
# Brazilian cruiser Rio Grande do Sul

Rio Grande do Sul was a Bahia-class cruiser built for the Brazilian Navy in 1909–10.

## Construction and commissioning

Rio Grande do Sul was part of a large 1904 naval building program by Brazil. Also planned as part of this were the two Minas Geraes-class dreadnoughts, ten Pará-class destroyers, three submarines and a submarine tender. With a design that borrowed heavily from the British Adventure-class scout cruisers, Rio Grande do Sul's keel was laid in 1907 in Armstrong Whitworth's Elswick, Newcastle upon Tyne yard. Construction took about a year and a half, and she was launched on 20 April 1909 with Madame A. M. Gomez Ferraz being the sponsor on behalf of Her Excellency Senhora Dr. Carlos Barbosa. As a class, Bahia and Rio Grande do Sul were the fastest cruisers in the world when they were commissioned, and the first in the Brazilian Navy to utilize steam turbines for propulsion.

## Endnotes

* 1 2 3 4 5 6 7 8 9 10 11 Scheina, "Brazil," 405.
* ↑ "Rio Grande do Sul 1910".
* 1 2 3 4 5 6 7 8 9 10 11 12 "Rio Grande do Sul I," Serviço de Documentação da Marinha – Histórico de Navios.
* 1 2 3 4 5 6 Moore ed., Janes Fighting Ships, 300.
* ↑ "Cruzador Bahia – C 12/C 2 Archived 26 February 2008 at the Wayback Machine" (in Portuguese), Navios de Guerra Brasileiros. Retrieved 8 November 2012.
* 1 2 Scheina, "Brazil," 403.
* ↑ Scheina, Latin America's Wars, 37.
* ↑ The Engineer. Vol. 107. 1909. p. 420.
# 2019 in Ecuador

Events in the year 2019 in Ecuador.

## Incumbents

* President of Ecuador - Lenín Moreno
* Vice President of Ecuador - Otto Sonnenholzner

## Events

* 13 June - The Supreme Court of Ecuador votes to legalize same-sex marriage
* 2019 Ecuadorian protests
# 1913 Australian referendum (Monopolies)

The Constitution Alteration (Nationalization of Monopolies) Bill 1912, was an unsuccessful referendum held in 1913 that sought to alter the Australian Constitution to give the Commonwealth legislative power in respect to monopolies.

## Question

Do you approve of the proposed law for the alteration of the Constitution entitled 'Constitution Alteration (Nationalization of Monopolies) 1912'?
The proposal was to alter the text of section 51 of the Constitution to read as follows:
   51a. (1) When each House of the Parliament, in the same session, has by resolution, passed by an absolute majority of its members, declared that the industry or business of producing, manufacturing, or supplying any specified services, is the subject of a monopoly, the Parliament shall have power to make laws for carrying on the industry or business by or under the control of the Commonwealth, and acquiring for that purpose on just terms any property used in connexion with the industry or business.
       (2) This section shall not apply to any industry or business conducted or carried on by the Government of a State or any public authority constituted under a State.

## Results

The referendum was not approved by a majority of voters, and a majority of the voters was achieved in only three states.
Result :
| State | Electoral roll | Ballots issued | For | For | Against | Against | Informal |
| State | Electoral roll | Ballots issued | Vote | % | Vote | % | Informal |
| New South Wales | 1,036,187 | 717,855 | 301,192 | 46.85 | 341,724 | 53.15 | 73,683 |
| Victoria | 830,391 | 626,861 | 287,379 | 49.07 | 298,326 | 50.93 | 40,828 |
| Queensland | 363,082 | 280,525 | 139,019 | 54.17 | 117,609 | 45.83 | 23,676 |
| South Australia | 244,026 | 195,463 | 91,411 | 51.26 | 86,915 | 48.74 | 16,920 |
| Western Australia | 179,784 | 132,149 | 64,988 | 53.19 | 57,184 | 46.81 | 9,644 |
| Tasmania | 106,746 | 80,398 | 33,176 | 45.22 | 40,189 | 54.78 | 6,907 |
| Total for Commonwealth | 2,760,216 | 2,033,251 | 917,165 | 49.33 | 941,947 | 50.67 | 171,658 |
| Results | Obtained majority in three states and an overall minority of 24,782 votes. Not carried | Obtained majority in three states and an overall minority of 24,782 votes. Not carried | Obtained majority in three states and an overall minority of 24,782 votes. Not carried | Obtained majority in three states and an overall minority of 24,782 votes. Not carried | Obtained majority in three states and an overall minority of 24,782 votes. Not carried | Obtained majority in three states and an overall minority of 24,782 votes. Not carried | Obtained majority in three states and an overall minority of 24,782 votes. Not carried |

## Discussion

The 1911 referendum asked a single question that dealt with the acquisition of monopolies. This resolution separated laws in relation to monopolies and the acquisition of monopolies into different questions. Like its forebear, neither resolution was carried. On each of the many occasions a similar question was asked at a referendum the public decided not to vest power in the Commonwealth over these matters.
* 1911 referendum on monopolies
# Asymmetric counteranion directed catalysis

Asymmetric counteranion directed catalysis (ACDC) or chiral anion catalysis in enantioselective synthesis is the "induction of enantioselectivity in a reaction proceeding through a cationic intermediate by means of ion pairing with a chiral, enantiomerically pure anion provided by the catalyst". Although chiral Brønsted acid catalyzed reactions may well fall into this category of catalysis under the definition given here (e.g., protonation of an imine by a chiral phosphoric acid), the extent of proton transfer and the demarcation between hydrogen bonding and full proton transfer is often ambiguous. Hence, some authors may exclude ion pair formation by proton transfer as a type of chiral counteranion catalysis. The discussion below will focus on chiral ion pairs generated through means other than proton transfer. (For a discussion about chiral Brønsted acid catalyzed reactions, see the article on hydrogen bond catalysis.)
The concept of utilizing the counteranion as the source of chirality in catalysis was first proposed by Arndtsen and coworkers in 2000, who applied chiral borate anions to copper-catalyzed olefin aziridination and cyclopropanation. The enantioselectivities observed were low: <10% ee in cases where the chiral borate was the only source of chirality. However, the observation that enantioinduction occurred only in nonpolar solvents supports the proposed role of the borate as the chiral counteranion.
The term asymmetric counteranion-directed catalysis was coined in 2006 by List in the context of organocatalytic iminium reduction in the presence of a chiral phosphate anion:
Chiral anions have been combined with homogeneous catalysts, illustrated by chiral phosphate anions for intramolecular allene hydrofunctionalization reactions catalyzed by phosphinegold(I) complexes:
Subsequently, Toste and coworkers advanced the concept of chiral anion phase transfer catalysis, in which phase segregation (solid/organic or aqueous/organic) is used as a tactic to enforce the pairing of a cationic reagent or intermediate with a chiral counteranion. In the example below, the fluorinating reagent Selectfluor exhibits extremely limited solubility in nonpolar solvents and is therefore unreactive as an insoluble bulk solid. Exchange of its tetrafluoroborate anions with two equivalents of a chiral, lipophilic phosphate anion brings the reagent into solution as an ion-triplet which behaves as a source of chiral "F$^+$":