Efficient Highly Selective Synthesis of Methyl 2-(Ethynyl)alk-2(E)-enoates and 2-(1′-Chlorovinyl)alk-2(Z)-enoates from 2-(Methoxycarbonyl)-2,3-allenols

被引：31

作者：

Deng, Youqian ^{[1
]}

Jin, Xin ^{[2
]}

Fu, Chunling ^{[1
]}

Ma, Shengming ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Lab Mol Recognit & Synth, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 10期

基金：

中国国家自然科学基金;

关键词：

STEREOSELECTIVE-SYNTHESIS; CONJUGATED ENYNES; COUPLING-CYCLIZATION; CROSS-METATHESIS; ELIMINATION-REACTIONS; CATALYZED SYNTHESIS; S(N)2' REACTIONS; ALPHA-ALLENOLS; PALLADIUM; DIENES;

D O I：

10.1021/ol9004273

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly regio- and stereoselective reactions of readily available 2-(methoxycarbonyl)-2,3-allenols 1 with oxalyl chloride in the presence of Et3N or DMSO afforded methyl 2-(ethynyl)alk-2(E)-enoates (E)-2 and 2-(1'-chlorovinyl)alk-2(Z)-enoates (Z)-3, respectively, in moderate to good yields.

引用

页码：2169 / 2172

页数：4

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