Dual Lewis acid-Lewis base activation in enantioselective cyanation of aldehydes using acetyl cyanide and cyanoformate as cyanide sources

被引：150

作者：

Lundgren, S ^{[1
]}

Wingstrand, E ^{[1
]}

Penhoat, M ^{[1
]}

Moberg, C ^{[1
]}

机构：

[1] Royal Inst Technol, Dept Chem Organ Chem, SE-10044 Stockholm, Sweden

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 33期

关键词：

D O I：

10.1021/ja052804q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dual activation by a chiral Lewis acid and an achiral or chiral Lewis base enabled cyanation of both aromatic and aliphatic aldehydes with acetyl cyanide and ethyl cyanoformate to provide direct access to O-acetylated and O-alkoxycarbonylated cyanohydrins, respectively, under mild conditions. With a combination of a Ti-salen catalyst and Et3N, benzaldehyde was converted to the O-acetylated cyanohydrin with 94% ee within 10 h at -40 °C in 89% isolated yield. Copyright © 2005 American Chemical Society.

引用

页码：11592 / 11593

页数：2

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