Diastereoselective reactions of δ-oxy-substituted allylic acetates with organocopper reagents

被引：20

作者：

Belelie, JL ^{[1
]}

Chong, JM ^{[1
]}

机构：

[1] Univ Waterloo, Guelph Waterloo Ctr Grad Work Chem & Biochem, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 09期

关键词：

D O I：

10.1021/jo016310x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

S(N)2'(gamma) substitutions of delta-substituted allylic acetates with Grignard reagents and copper catalysts proceed with high diastereoselectivities. With benzyloxy, methoxymethoxy, and tert-butyldimethylsiloxy groups, reactions favor the anti-isomer with selectivities up to anti:syn = >99:1. With a hydroxyl group, selectivities are reversed and the syn-isomer is favored with selectivities up to anti:syn = <1:99.

引用

页码：3000 / 3006

页数：7

共 31 条

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[2]

[Anonymous], 1994, ORGANOMETALLICS SYNT

[3]

[Anonymous], 1997, ORG REACT

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