DIASTEREODIFFERENTIATION IN SN2' ADDITIONS OF METHYLCUPRATES TO NONRACEMIC ACYCLIC VINYLOXIRANES

被引：34

作者：

MARSHALL, JA

BLOUGH, BE

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 06期

关键词：

D O I：

10.1021/jo00006a049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

S(N)2' additions of Me2CuLi, MeCu(CN)Li, and Me2Cu(CN)Li2 to the 2S and 2R alkoxy cis-(Z)- and -(E)- vinyloxiranes 8, 9, 13, and 14 were examined as possible routes to acrylic subunits of polypropionate natural products. Highest antisyn ratios were found for the (2S)- and (2R)-hydroxy-(E)-vinyloxiranes 13a and 14a followed by the (2R)-MTM ether analogue 14c. In both cases Me2CuLi gave higher ratios than either of the cyanocuprates (> 99:1 vs 14:1 for 13a/13b and > 40:1 vs approximately 24:1 for 14c).

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页码：2225 / 2234

页数：10

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