Regio- and stereo-selective synthesis of tetrasubstituted olefins by the three-component tandem reaction of phenylselenomagnesium bromide, acetylenic sulfones and allylic bromides

被引：2

作者：

Huang, Bin ^{[1
]}

You, Shengyong ^{[2
]}

Cai, Mingzhong ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Dept Chem, Nanchang 330022, Peoples R China

[2] Jiangxi Acad Sci, Inst Appl Chem, Nanchang 330029, Peoples R China

来源：

JOURNAL OF CHEMICAL RESEARCH | 2010年 / 03期

基金：

中国国家自然科学基金;

关键词：

acetylenic sulfone; Michael addition; vinyl sulfone; vinyl selenide; tetrasubstituted olefin; MAGNESIUM EXCHANGE; SELENIDES; CATALYST; ADDUCTS;

D O I：

10.3184/030823410X12670432614319

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tetrasubstituted olefins containing a 1,4-diene structural unit can be regio- and stereo-selectively synthesised in good yields under mild conditions, in one pot, by Michael addition of phenylselenomagnesium bromide to acetylenic sulfones, followed by coupling with allylic bromides.

引用

页码：127 / 129

页数：3

共 31 条

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Xie, MH
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ORGANIC LETTERS, 2006, 8 (03) : 431 - 434
[2] Regio- and stereoselective synthesis of tetrasubstituted allylic alcohols by three-component reaction of acetylenic sulfone, dialkylzinc, and aldehyde
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[4] REGIO-SELECTIVE AND STEREO-SELECTIVE GAMMA-SUBSTITUTION OF ALLYLIC SULFOXIDES AND SULFONES WITH LITHIUM DIALKYLCUPRATES - A NEW SYNTHESIS OF TRISUBSTITUTED OLEFINS
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JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25): : 8895 - 8900
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TETRAHEDRON LETTERS, 2015, 56 (17) : 2214 - 2218
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[10] Reaction of (Z)-1-bromoalk-1-enyldialkylboranes with DMSO:: regio- and stereo-selective formation of internal (E)-alkenyl bromides
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