SN2-type ring opening of substituted-N-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt

被引：0
作者：
Ghorai, Manas K. [1 ]
Tiwari, Deo Prakash [1 ]
Kumar, Amit [1 ]
Das, Kalpataru [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
JOURNAL OF CHEMICAL SCIENCES | 2011年 / 123卷 / 06期
关键词：
Haloamines; aziridines; enantioselective; Lewis acid; nucleophilic ring opening; quaternary ammonium salts; STEREOSELECTIVE AMINOHALOGENATION; TETRABUTYLAMMONIUM HALIDES; ACTIVATED AZIRIDINES; EFFICIENT APPROACH; MESO-AZIRIDINES; FORMAL 3+2; REARRANGEMENT; EPOXIDES; FACILE; CYCLOADDITION;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Quaternary ammonium salt mediated highly regioselective ring opening of aziridines with zinc(II) halides to racemic and non-racemic beta-halo amines in excellent yield and selectivity is described. The reaction proceeds via an S(N)2-type pathway and the partial racemization of the starting substrate and the product was effectively controlled by using quaternary ammonium salts to afford the enantioenriched products (er up to 95:5).
引用
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页码：951 / 961
页数：11
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