On the diastereoselectivity of alkylations of bicyclic lactams

被引：34

作者：

Bailey, JH

Byfield, ATJ

Davis, PJ

Foster, AC

Leech, M

Moloney, MG

Müller, M

Prout, CK

机构：

[1] Univ Oxford, Dyson Perrins Lab, Dept Chem, Oxford OX1 3QY, England

[2] Univ Oxford, Chem Crystallog Lab, Oxford OX1 3PD, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 12期

关键词：

D O I：

10.1039/b000432o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselectivity in the alkylation of the enolates of bicyclic lactams 2 derived from pyroglutaminol 1a has been found to depend upon the nature of the hemiaminal ether protecting group. Although exo-alkylation has been widely reported for 2a,b,e, endo-alkylation is favoured for 2d. It is postulated that this is a result of the opening of the bicyclic structure of the enolate derived from 2d, and the consequent stereoelectronic facilitation of endo-facial attack.

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页码：1977 / 1982

页数：6

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