ENANTIOSELECTIVE PREPARATION OF BETA-ALKYL-GAMMA-BUTYROLACTONES FROM FUNCTIONALIZED KETENE DITHIOACETALS

被引：130

作者：

KOCH, SSC ^{[1
]}

CHAMBERLIN, AR ^{[1
]}

机构：

[1] UNIV CALIF IRVINE, DEPT CHEM, IRVINE, CA 92717 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 10期

关键词：

D O I：

10.1021/jo00062a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and general enantioselective synthesis of beta-alkyl-gamma-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity. Reductive removal of the chiral auxiliary followed by acid-induced cyclization of the resultant hydroxy ketene dithioacetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.

引用

页码：2725 / 2737

页数：13

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[91] ENZYMES IN ORGANIC-SYNTHESIS .24. PREPARATIONS OF ENANTIOMERICALLY PURE CHIRAL LACTONES VIA STEREOSPECIFIC HORSE LIVER ALCOHOL-DEHYDROGENASE CATALYZED OXIDATIONS OF MONOCYCLIC MESO DIOLS [J].