Ortho-[2,3]-Wittig rearrangement of benzyl propargyl ethers:: Striking preference over the competing [1,2]-Wittig shift

被引：7

作者：

Tomooka, K ^{[1
]}

Harada, M ^{[1
]}

Hanji, T ^{[1
]}

Nakai, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 1528552, Japan

来源：

CHEMISTRY LETTERS | 2000年 / 12期

关键词：

D O I：

10.1246/cl.2000.1394

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of benzyl gamma-(trimethylsilyl)propargyl ether with n-BuLi is shown to afford the rarely precedent ortho-[2,3]-Wittig product in remarkable preference to the [1,2]-Wittig product. The factors governing the periselectivity in this type of carbanion rearrangement are discussed.

引用

页码：1394 / 1395

页数：2

共 13 条

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[9] 2-5
[10] [1,2]-WITTIG REARRANGEMENT OF ENANTIO-DEFINED ALPHA-ALKOXYALKYLLITHIUMS - STRUCTURAL REQUIREMENT AND STERIC COURSE AT THE LI-BEARING TERMINUS
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IGARASHI, T
NAKAI, T
[J]. TETRAHEDRON, 1994, 50 (20) : 5927 - 5932

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