[2,3] WITTIG REARRANGEMENT OF NONRACEMIC PROPARGYLOXYACETIC ACIDS AND ESTERS - SYNTHESIS OF OPTICALLY-ACTIVE 2,5-DIHYDROFURANS

被引：74

作者：

MARSHALL, JA

WANG, XJ

机构：

[1] Department of Chemistry, The University of South Carolina, Columbia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期

关键词：

D O I：

10.1021/jo00297a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: Optically active propargyloxyacetic acids 4, available in ca. 90% ee through reduction of alkynones 2 with Chirald-LiAlH4followed by alkylation with chloroacetic acid, undergo highly stereoselective [2,3] rearrangement upon treatment with LDA in THF at -78 °C to afford α-(S)-hydroxy-β-(R)-allenic acids with complete transfer of chirality and >90% diastereoselectivity. The diastereomeric methyl ester derivatives 5a and 13 cyclize stereospecifically to trans and cis 1,5-dihydrofurans upon treatment with AgN03-CaC03, PhSeCl, or NBS. © 1990, American Chemical Society. All rights reserved.

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页码：2995 / 2996

页数：2

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