Synthesis and anionically induced domino reactions of chiral α-bromo α,β-unsaturated esters

被引：0

作者：

Braun, NA ^{[1
]}

Burkle, U ^{[1
]}

Feth, MP ^{[1
]}

Klein, I ^{[1
]}

Spitzner, D ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Chem, D-70599 Stuttgart, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 1998卷 / 08期

关键词：

asymmetric dihydroxylation (Sharpless-AD); Wittig olefination; alpha-bromo alpha; beta-unsaturated esters; diastereoselective aprotic Michael domino reaction; tricyclo[3.2.1.0(2,7)] octanes;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral alpha-bromo alpha,beta-unsaturated esters 3 and 9 are prepared by asymmetric Sharpless dihydroxylation (AD) of 5 and from ester 7 and the chiral diols 8 by transacetalization, respectively. Both types of alpha-bromo alpha,beta-unsaturated ester react with the kinetic Lithium dienolates of enone 10 to give functionalized tricyclo[3.2.1.0(2,7)]octanes 11. Esters 3 give one single diastereomer (de greater than or equal to 95%), whereas mixtures of diastereomers (de 28 to 46%) are obtained with the esters 9.

引用

页码：1569 / 1576

页数：8

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