Reversal of enantioselectivity by catalyst protonation: Asymmetric hydrocyanation of imines with oxazaborolidines

被引：33

作者：

Berkessel, A ^{[1
]}

Mukherjee, S ^{[1
]}

Lex, J ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

SYNLETT | 2006年 / 01期

关键词：

oxazaborolidine; asymmetric catalysis; hydrocyanation; imine; protonation;

D O I：

10.1055/s-2005-922757

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new application of chiral oxazaborolidines in asymmetric transformation, namely the hydrocyanation of imines, is described. The effect of protonation of these catalysts on the reactivity and enantioselectivity of hydrocyanations is studied. Significant increase in reaction rate is observed upon protonation of the catalysts, along with the reversal of the sense of stereoinduction.

引用

页码：41 / 44

页数：4

共 32 条

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