The effects of different ester and ketal protecting groups on the reactivity and selectivity of tartrate-derived silylketene acetals

被引：10

作者：

Aggarwal, VK

Masters, SJ

Adams, H

Spey, SE

Brown, GR

Foubister, AJ

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] Zeneca Pharmaceut, Macclesfield SK10 4TG, Cheshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 02期

关键词：

D O I：

10.1039/a807863g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of tartrate-derived silylketene acetals and benzaldehyde has been investigated and the yields and diastereoselectivities have been found to be dependent upon the nature of the tartrate ester. Utilising the di-tert-butyl tartrate derivatives, high yields were achieved using a variety of aldehyde substrates. The reactions all proceeded with excellent levels of stereoselectivity (greater than or equal to 82:18); the sense of induction being dependent upon the choice of Lewis acid. BF3. OEt2 and TiCl3((OPr)-Pr-i) furnished complementary products in several cases and a model has been proposed to account for this observation.

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页码：155 / 162

页数：8

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