Recent Developments in Asymmetric Organocatalytic Domino Reactions

Abstract

AbstractSince about the year 2000, the research area of asymmetric organocatalysis has grown rapidly to become one of the most fascinating and current fields in organic chemistry. In the last years, asymmetric domino reactions have widely benefited from this fast‐growing field, as exemplified by the development of an explosive number of novel and powerful asymmetric organocatalytic domino processes, which allowed the easy construction of complex chiral molecular architectures from simple materials with high yields and very often remarkable enantioselectivities in a metal‐free environment. Indeed, the possibility to join two or more organocatalytic reactions in one asymmetric domino process has become a challenging goal for chemists, due to several advantages from economical and environmental points of view, avoiding costly protecting groups and time‐consuming purification procedures after each step, for example. This review aims to update the latest developments of this hot and fascinating field, covering the literature since the beginning of 2009. Abbreviations:Ac: acetyl; Ar: aryl; BDHP: 1,1′‐binaphth‐2,2′‐diyl hydrogen phosphate; BA: Brønsted acid; BINAPO: 2‐diphenylphosphino‐2′‐diphenylphosphinyl‐1,1′‐binaphthalene; BINOL: 1,1′‐bi‐2‐naphthol; Boc:tert‐butoxycarbonyl; Bn: benzyl; Bu: butyl; Bz: benzoyl; CSA: camphorsulfonic acid; Cy: cyclohexyl; Cbz: benzyloxycarbonyl; DABCO: 1,4‐diazabicyclo[2.2.2]octane; DBU: 1,8‐diazabicyclo[5.4.0]undec‐7‐ene; DCE: dichloroethane;de: diastereomeric excess; DFT: density functional theory; DHQ: hydroquinine; DHQD: dihydroquinidine; DIPEA: diisopropylethylamine; DKR: dynamic kinetic resolution; DMAD: dimethyl acetylenedicarboxylate; E: electrophile;ee: enantiomeric excess; ESI: electrospray ionization; Et: ethyl; Fu: furyl; Hept: heptyl; Hex: hexyl; HOMO: highest occupied molecular orbital; IBX:o‐iodoxybenzoic acid; LB: Lewis base; LUMO: lowest unoccupied molecular orbital; Me: methyl; MOM: methoxymethyl; Mes: mesyl; MS: mass spectroscopy; MTBE: methyltert‐butyl ether; NADH: nicotinamide adenine dinucleotide; Naph: naphthyl; NHC: N‐heterocyclic carbene; NMM:N‐methylmorpholine; NMP:N‐methylpyrrolidinone; Ns: nosyl; Nu: nucleophile; Oct: octyl; PCC: pyridinium chlorochromate; Pent: pentyl; PFBA: pentafluorobenzoic acid; Ph: phenyl; PMB:para‐methoxybenzyl; Pr: propyl; Py: pyridine; r.t.: room temperature; TBA: tribromoacetic acid; TBS:tert‐butyldimethylsilyl; TCBA: 2,4,6‐trichlorobenzoic acid; TES: triethylsilyl; TFA: trifluoroacetic acid; THF: tetrahydrofuran; Thio: thiophene; TMEDA: tetramethylethylenediamine; TMS: trimethylsilyl; Tol: tolyl; Ts: 4‐toluenesulfonyl (tosyl).