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A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs

Guobi Chai, Shangze Wu, Chunling Fu and Shengming Ma*

*Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P.R. China, Email: masmsioc.ac.cn

G. Chai, S. Wu, C. Fu, S. Ma, J. Am. Chem. Soc., 2011, 133, 3740-3743.

DOI: 10.1021/ja1108694 (free Supporting Information)



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Abstract

A tandem Michael addition/cyclic 1,2-addition/elimination of 2,3-allenoates and organozinc reagents enables the synthesis of polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain. Application to the synthesis of stereodefined β,γ-unsaturated enones is demonstrated.

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Key Words

Cyclobutenones


ID: J48-Y2011-0680