Asymmetric dihydroxylation of vinyl sulfones:: routes to enantioenriched α-hydroxyaldehydes and the enantioselective syntheses of furan-2(5H)-ones

被引：47

作者：

Evans, P ^{[1
]}

Leffray, M ^{[1
]}

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

来源：

TETRAHEDRON | 2003年 / 59卷 / 40期

关键词：

asymmetric dihydroxylation; vinyl sulfones; prochiral alkene; alpha-hydroxyaldehydes;

D O I：

10.1016/j.tet.2003.08.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric dihydroxylation of alpha,beta-unsaturated sulfones under Sharpless conditions affords enantioenriched alpha-hydroxyaldehydes in a complex mixture of dimeric species. These mixtures undergo olefination generating the corresponding alpha,beta-unsaturated esters or furan-2(5H)-ones with high levels of enantiomeric excess. The application of this method for the rapid stereoselective synthesis of the furanone natural products; quercus lactone and maritolide, are described. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7973 / 7981

页数：9

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