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

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• 作者：Guobi Chai ; Shangze Wu ; Chunling Fu ; Shengming Ma
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：March 23, 2011
• 年：2011
• 卷：133
• 期：11
• 页码：3740-3743
• 全文大小：803K
• 年卷期：v.133,no.11(March 23, 2011)
• ISSN：1520-5126

文摘

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 尾,纬-unsaturated enones is demonstrated.