Highly diastereoselective syntheses of propargylic acid and homopropargylic systems

被引：28

作者：

Ferreira, F ^{[1
]}

Denichoux, A ^{[1
]}

Chemla, F ^{[1
]}

Bejjani, J ^{[1
]}

机构：

[1] Univ Paris 06, Chim Organ Lab, UMR 7611, F-75252 Paris 05, France

来源：

SYNLETT | 2004年 / 12期

关键词：

aziridines; carbenoids; epoxides; homopropargylic alcohols; zinc;

D O I：

10.1055/s-2004-832816

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The results of our research dealing with the stereoselective synthesis of propargylic and homopropargylic systems are summarized. In a first part, the stereoselective formation of syn- or anti-disubstituted homopropargylic alcohols from acetylenic oxiranes through S(N)2 or double S(N)2' has been developed. Thus, the two diastereomers of a given homopropargylic alcohol are stereospecifically available. The great impact of Lewis acid activation on the regioselectivity of the ring-opening reactions of propargylic oxiranes is also detailed. In a second part, the preparation and uses of new acetylenic/allenic carbenoids are overviewed; their reactivity towards carbonyl compounds and imines is examined, leading to the highly stereoselective synthesis of acetylenic chlorohydrins, oxiranes and aziridines.

引用

页码：2051 / 2065

页数：15

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