Configurational stability and stereospecificity in the reactions of amide-stabilised organolithiums: A non-stereospecific tin-lithium exchange

被引：38

作者：

Clayden, J

Pink, JH

机构：

[1] Department of Chemistry, University of Manchester, Manchester, M13 9PL, Oxford Road

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 14期

关键词：

CHIRAL ORGANOMETALLIC REAGENTS; SUBSTITUTIONS; (-)-SPARTEINE;

D O I：

10.1016/S0040-4039(97)00402-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoisomers of laterally lithiated tertiary naphthamides are configurationally stable at the lithium-bearing stereogenic centre at -40 degrees C, The syn diastereoisomer, which may be formed by stereoselective deprotonation or stereospecific transmetallation, reacts stereospecifically, but both the tin-lithium exchange leading to the anti diastereoisomer and its subsequent reactions are characterised by an unprecedented lack of stereospecificity. (C) 1997 Elsevier Science Ltd.

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页码：2565 / 2568

页数：4

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