Electronic effect on the regioselectivity in the ring opening of para-substituted phenyloxiranes by acetylides

被引：13

作者：

Shindo, M ^{[1
]}

Sugioka, T ^{[1
]}

Shishido, K ^{[1
]}

机构：

[1] Univ Tokushima, Grad Sch, Inst Hlth Biosci, Tokushima 7708505, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 50期

关键词：

oxirane; alkynylation; regioselectivity; electronic effect; Lewis acid;

D O I：

10.1016/j.tetlet.2004.10.049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electronic effect on the regioselectivity in the alkynylation of phenyloxiranes was investigated using three kinds of metal acetylides. BF3 mediated lithium acetylide provided either the alpha- or beta-alkynylated products by controlling the effect of the para-substituents of the phenyloxiranes. LiClO4 mediated lithium acetylide and titanium acetylide, on the other hand, afforded predominantly the beta- and alpha-products, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：9265 / 9268

页数：4

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