Diastereoselective reactions of enolates

被引：12

作者：

Braun, M

Sacha, H

Galle, D

Baskaran, S

机构：

[1] Institut für Organische Chemie, Universität Düsseldorf

来源：

PURE AND APPLIED CHEMISTRY | 1996年 / 68卷 / 03期

关键词：

D O I：

10.1351/pac199668030561

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Triphenylglycol-derived esters 2 and 8a have been applied in asymmetric aldol reactions. The homochiral propionates 7 and 8a,b react with imines ina stereodivergent manner: Doubly deprotonated 7 delivers anti-beta-lactams 14 whereas the lithium enolates of 8a/b afford cis-beta-lactams 15 in 87-97% e.e. Diastereoselective carbon silylation occurs when deprotonated 8a is treated with chlorotrimethylsilane. Approaches towards the construction of quaternary carbon centers are based on diastereoselective carboxalkylations of enolates with menthylchloroformate 17 and on a novel tandem reaction (16 --> 20).

引用

页码：561 / 564

页数：4

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