Highly stereoselective kinetic enolate formation: Steric vs electronic effects

被引：45

作者：

Xie, LF

Isenberger, KM

Held, G

Dahl, LM

机构：

[1] Department of Chemistry, University of Wisconsin, Oshkosh

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 21期

关键词：

D O I：

10.1021/jo971260a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The utility of enolates has been well exemplified by their applications in the synthesis of many biologically important natural products via aldol condensation reactions. Since specific biological activities of many natural products are regulated by their stereochemistry, excellent stereoselection during their synthesis is highly demanded. Previous studies have shown that kinetic aldol diastereoselectivity depends to a large degree on the geometry (cis or trans) of preformed enolates. Among many lithium amides used in kinetic enolate formation, the most popular ones include lithium diisopropylamide (LDA), lithium tetramethylpiperidide (LTMP), and lithium hexamethyldisilazide (LHMDS). Through their elegant work with ethyl ketones, Heathcock and co-workers have reported the stereoselectivity of kinetic enolization of many ketones with these bases. © 1997 American Chemical Society.

引用

页码：7516 / 7519

页数：4

共 30 条

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