Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides

被引：22

作者：

Clayden, J

Westlund, N

Frampton, CS

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[2] Roche Discovery Welwyn, Welwyn Garden City AL7 3AY, Herts, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 09期

关键词：

D O I：

10.1039/b000670j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Restricted rotation about the Ar-CO bond means that 1-naphthamides bearing chiral 8-substituents may exist as pairs of diastereoisomeric atropisomers. These atropisomers are formed with good to excellent stereoselectivity for the syn-diastereoisomer by the reaction of 8-formyl-1-naphthamides with organolithiums and Grignard reagents. The reduction of 8-acyl-1-naphthamides also proceeds with syn-selectivity. The product alcohols are prone to lactonisation and also to epimerisation, and some of the apparent diastereoselectivities may be the result of thermodynamic, rather than kinetic, control.

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页码：1379 / 1385

页数：7

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