Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids.: Applications in Wittig reactions and heterocycle synthesis

被引：53

作者：

Davies, SB ^{[1
]}

McKervey, MA ^{[1
]}

机构：

[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(98)02573-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Z-gamma-amino alcohols derived from nonracemic beta-amino acids are smoothly oxidised by manganese dioxide in acetonitrile to afford aldehydes which can be trapped in situ in Wittig reactions with carbonyl-substituted phosphoranes. The application of this methodology to the synthesis of the alkaloids (S)-(+)-N-BOC-coniine, (S)-(-)-coniceine and a pipecoline precursor is described. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：1229 / 1232

页数：4

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