A straightforward synthesis of cyclobutenones via a tandem Michael addition/cyclization reaction of 2,3-allenoates with organozincs |
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Authors: | Chai Guobi Wu Shangze Fu Chunling Ma Shengming |
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Institution: | Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China. |
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Abstract: | 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 β,γ-unsaturated enones is demonstrated. |
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