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
收藏
页码：1229 / 1232
页数：4
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