Bifunctional Asymmetric Catalysis with Hydrogen Chloride: Enantioselective Ring Opening of Aziridines Catalyzed by a Phosphinothiourea

被引：48

作者：

Mita, Tsuyoshi ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

SYNLETT | 2009年 / 10期

基金：

日本学术振兴会;

关键词：

asymmetric catalysis; halogenation; ring opening; carbocations; aziridines; PYRIDINE N-OXIDES; PICTET-SPENGLER REACTIONS; CHIRAL LEWIS-BASE; MESO-AZIRIDINES; KINETIC RESOLUTION; SILICON TETRACHLORIDE; TERMINAL EPOXIDES; BOND DONORS; COMPLEXES; DESYMMETRIZATION;

D O I：

10.1055/s-0029-1217344

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring opening of aziridines with hydrogen chloride to form beta-chloroamine derivatives is catalyzed by a chiral phosphinothiourea derivative in high yields and with high enantioselectivities. On the basis of P-31 NMR studies, activation of HCl appears to proceed via quantitative protonation of the catalyst to afford a phosphonium chloride complex.

引用

页码：1680 / 1684

页数：5

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