Recent Developments in Asymmetric Aziridination

This review updates the recent developments in asymmetric aziridination using chiral substrates as well as chiral catalysts, covering the literature since the beginning of 2010. It clearly demonstrates that this reaction constitutes an important tool in organic synthesis, still attracting considerable interest due to the potential use of enantiopure aziridines as useful intermediates in the synthesis of complex important molecules, and to the intriguing biological activities of numerous aziridine‐containing compounds including natural products. Abbreviations: Ar: aryl; BINOL: 1,1′‐bi‐2‐naphthol; Bn: benzyl; Boc: tert ‐butoxycarbonyl; BUDAM: tetra‐ tert‐ butyldianisylmethyl; Bz: benzoyl; Cbz: benzyloxycarbonyl; Cy: cyclohexyl; DAM: dianisylmethyl; DBN: 3,5‐dinitrobenzoyl; DCE: 1,2‐dichloroethane; de : diastereomeric excess; DEAD: diethyl azodicarboxylate; DIAD: diisopropyl azodicarboxylate; DMAP: 4‐dimethylaminopyridine; DMF: N,N ‐dimethylformamide; DMSO: dimethyl sulfoxide; dr : diastereomeric ratio; ee : enantiomeric excess; esp: α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropionate; FG: functional group; Hex: hexyl; HMDS: hexamethyldisilazide; LDA: lithium diisopropylamide; M: metal; MEDAM: tetramethyldianisylmethyl; MEDPM: tetramethyldiphenylmethyl; Mes: mesyl; MS: molecular sieves; Naph: naphthyl; NCS: N‐ chlorosuccinimide; Ns: nosyl; PG: protecting group; Phth: phthalimido; Piv: pivalate; PMB: para ‐methoxybenzoyl; PMP: para ‐methoxyphenyl; PNNP: N,N′ ‐bis[ ortho ‐(diphenylphosphino)benzylidene]cyclohexane‐1,2‐diamine; r.t.: room temperature; SES: trimethylsilylethanesulfonyl; TBS: tert ‐butyldimethylsilyl; TEA: triethylamine; Tf: trifluoromethanesulfonyl; TFA: trifluoroacetic acid; THF: tetrahydrofuran; TMG: 1,1,3,3‐tetramethylguanidine; TMS: trimethylsilyl; Tol: tolyl; TPS: triphenylsilyl; Troc: 2,2,2‐trichloroethoxycarbonyl; Ts: 4‐toluenesulfonyl (tosyl). magnified image