4.8 Article

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

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 11, 页码 3740-3743

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AMER CHEMICAL SOC
DOI: 10.1021/ja1108694

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资金

  1. National Basic Research Program of China [2009CB825300]
  2. National Natural Science Foundation of China [20732005, J0830413]

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An efficient method for synthesis of polysubstituted cyclobutenones, which are not readily available from traditional methods due to the intrinsic ring strain, is described. The reaction of 2,3-allenoates and organozinc reagents proceeds via a tandem Michael addition/cyclic 1,2-addition/elimination mechanism with the functional groups from the organozinc reagents being introduced to the 3-position of the cyclobutenone products regiospecifically in moderate to excellent yields. Application to the synthesis of stereodefined beta,gamma-unsaturated enones is demonstrated.

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