An easy access to enantio-enriched α-substituted aldehydes by carbolithiation of β-phenyl or β-silyl-α,β-ethylenic aldehydes, protected with the monolithioamide of a chiral diamine

被引：15

作者：

Brémand, N ^{[1
]}

Mangeney, P ^{[1
]}

Normant, JF ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, Lab Chim Organoelements, F-75252 Paris 05, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 10期

关键词：

aldehyde; carbometalation; diastereoselection;

D O I：

10.1016/S0040-4039(01)00034-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium amide derived from N,N,N'-trimethyl-l,2-diphenylethanediamine converts cinnamaldehyde to a lithium alkoxyamide which undergoes a regio- and stereoselective carbolithiation upon addition of various organolithiums. Subsequent hydrolysis or trapping with MeI delivers alpha -mono-, or alpha,beta -disubstituted 3-phenylpropanals with e.e.s of 76-96%. Extension to a silylated alpha -enal is possible. (C) 2001 Published by Elsevier Science Ltd.

引用

页码：1883 / 1885

页数：3

共 12 条

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