Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions
Authors: Clavier Hervé , Pellissier Hélène 
Published: November 2012

AbstractSince the first definition of domino reactions by Tietze in 1993, an explosive number of these fascinating reactions has been developed, allowing the easily building of complex chiral molecular architectures from simple materials to be achieved in a single step. Even more interesting, the possibility to join two or more reactions in one asymmetric domino process catalyzed by chiral metal catalysts has rapidly become one challenging goal for chemists, due to economical advantages, such as avoiding costly protecting groups and time‐consuming purification procedures after each step. The explosive development of enantioselective metal‐catalyzed domino including multicomponent reactions is a consequence of the considerable impact of the advent of asymmetric transition metal catalysis. This review aims to update the last developments of enantioselective one‐, two‐ and multicomponent domino reactions mediated by chiral metal catalysts, covering the literature since the beginning of 2006. Abbreviations: Ac: acetyl; AQN: anthraquinone; Ar: aryl; bdpp: 2,4‐bis(diphenylphosphino)pentane; BINAP: 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl; BINEPINE: phenylbinaphthophosphepine; BINIM: binapthyldiimine; BINOL: 1,1′‐bi‐2‐naphthol; BIPHEP: 2,2′‐bis(diphenylphosphino)‐1,1′‐biphenyl; Bn: benzyl; Boc: tert‐butoxycarbonyl; Box: bisoxazoline; BOXAX: 2,2′‐bis(oxazolyl)‐1,1′‐binaphthyl; BPTV: N‐benzene‐fused phthaloyl‐valine; Bu: butyl; Bz: benzoyl; Cat: catechol; Chiraphos: 2,3‐bis(diphenylphosphine)butane; cod: cyclooctadiene; Cy: cyclohexyl; DABCO: 1,4‐diazabicyclo[2.2.2]octane; dba: (E,E)‐dibenzylideneacetone; DBU: 1,8‐diazabicyclo[5.4.0]undec‐7‐ene; DCE: dichloroethane; de: diastereomeric excess; DHQ: hydroquinine; DHQD: dihydroquinidine; DIFLUORPHOS: 5,5′‐bis(diphenylphosphino)‐2,2,2′,2′‐tetrafluoro‐4,4′‐bi‐1,3‐benzodioxole; DIPEA: diisopropylethylamine; DMF: dimethylformamide; DMSO: dimethyl sulfoxide; DOSP: N‐p‐dodecylbenzenesulfonylprolinate; DPEN: 1,2‐diphenylethylenediamine; dtb: di‐tert‐butyl; dtbm: di‐tert‐butylmethoxy; E: electrophile; ee: enantiomeric excess; Et: ethyl; FBIP: ferrocene bis‐imidazoline bis‐palladacycle; Fc: ferrocenyl; FOXAP: ferrocenyloxazolinylphosphine; Hex: hexyl; HFIP: hexafluoroisopropyl alcohol; HMPA: hexamethylphosphoramide; iPr‐DuPhos: 1,2‐bis(2,5‐diisopropylphospholano)benzene; Josiphos: 1‐[2‐(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine ethanol adduct; L: ligand; MCPBA: 3‐chloroperoxybenzoic acid; Me: methyl; Me‐DuPhos: 1,2‐bis(2,5‐dimethylphospholano)benzene; MEDAM: bis(dimethylanisyl)methyl; MOM: methoxymethyl; Naph: naphthyl; NMI: N‐methylimidazole; MWI: microwave irradiation; Norphos: 2,3‐bis(diphenylphosphino)‐bicyclo[2.2.1]hept‐5‐ene; Ns: nosyl (4‐nitrobenzene sulfonyl); Nu: nucleophile; Oct: octyl; Pent: pentyl; Ph: phenyl; PHAL: 1,4‐phthalazinediyl; Pin: pinacolato; PINAP: 4‐[2‐(diphenylphosphino)‐1‐naphthalenyl]‐N‐[1‐phenylethyl]‐1‐phthalazinamine; Pr: propyl; Py: pyridyl; PYBOX: 2,6‐bis(2‐oxazolyl)pyridine; QUINAP: 1‐(2‐diphenylphosphino‐1‐naphthyl)isoquinoline; QUOX: quinoline‐oxazoline; Segphos: 5,5′‐bis(diphenylphosphino)‐4,4′‐bi‐1,3‐benzodioxole; Solphos: 7,7′‐bis(diphenylphosphino)‐3,3′,4,4′‐tetrahydro‐4,4′‐dimethyl‐8,8′‐bis‐2H‐1,4‐benzoxazine; SPRIX: spirobis(isoxazoline); SYNPHOS: 6,6′‐bis(diphenylphosphino)‐2,2′,3,3′‐tetrahydro‐5,5′‐bi‐1,4‐benzodioxin; Taniaphos: [2‐diphenylphosphinoferrocenyl](N,N‐dimethylamino)(2‐diphenylphosphinophenyl)methane; TBS: tert‐butyldimethylsilyl; TC: thiophene carboxylate; TCPTTL: N‐tetrachlorophthaloyl‐tert‐leucinate; TEA: triethylamine; Tf: trifluoromethanesulfonyl; TFA: trifluoroacetic acid; THF: tetrahydrofuran; TMS: trimethylsilyl; Tol: tolyl; Ts: 4‐toluenesulfonyl (tosyl); C3‐Tunephos: 1,13‐bis(diphenylphosphino)‐7,8‐dihydro‐6H‐dibenzo[f,h][1,5]dioxonin; VAPOL: 2,2′‐diphenyl‐[3,3′‐biphenanthrene]‐4,4′‐diol