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

Youqian Deng, Xin Jin, Chunling Fu and Shengming Ma*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China, Email: masmmail.sioc.ac.cn

Y. Deng, X. Kin, C. Fu, S. Ma, Org. Lett., 2009, 11, 2169-2172.

DOI: 10.1021/ol9004273

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Abstract

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

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Key Words

Enynes, Dienes, Vinyl Chlorides, Oxalyl Chloride, Dimethyl Sulfoxide

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ID: J54-Y2009-1610