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Synthesis 2009(3): 424-430  
DOI: 10.1055/s-0028-1083323
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© Georg Thieme Verlag Stuttgart ˙ New York

High Regio- and Stereoselective Synthesis of (Z)- or (E)-N-Acryl Butenedioic Monoimide Derivatives by a Multicomponent Reaction

Feng Shaa, Ying Lina, Xian Huang*a,b
a Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou 310028, P. R. of China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, P. R. of China
Fax: +86(571)88807077; e-Mail: huangx@mail.hz.zj.cn;
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Publication History

Received 11 September 2008
Publication Date:
09 January 2009 (online)

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Abstract

An efficient synthesis of (Z)- or (E)-N-acryl butenedioic monoimide derivatives with high regio- and stereoselectivity by the multicomponent reaction of acetylenic esters/ketones, isocyanides, and carboxylic acids is described. The E-isomers, obtained in high yields via E/Z isomerization, are also reported.

Key words

high regio- and stereoselectivity - multicomponent reactions - isocyanides - acetylenic esters/ketones - N-acryl butenedioic monoimides

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10

The crystal structure of 4f has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 696375. The data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].

13

It is interesting to note that the reactions exclusively gave the products possessing the Z-stereochemistry (Table  [²] ). For more information about this type of intermediates, see references 5a, 5b, and 5e.