A Computationally Designed Rh(I)-Catalyzed Two-Component [5+2+1] Cycloaddition of Ene-vinylcyclopropanes and CO for the Synthesis of Cyclooctenones

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• 作者：Yuanyuan Wang ; Jingxin Wang ; Jiachun Su ; Feng Huang ; Lei Jiao ; Yong Liang ; Dazhi Yang ; Shiwei Zhang ; Paul A. Wender ; Zhi-Xiang Yu
• 刊名：Journal of the American Chemical Society
• 出版年：2007
• 出版时间：August 22, 2007
• 年：2007
• 卷：129
• 期：33
• 页码：10060 - 10061
• 全文大小：57K
• 年卷期：v.129,no.33(August 22, 2007)
• ISSN：1520-5126

文摘

Through the combined use of computational (density functional theory) and experimental studies, a new [Rh(CO)₂Cl]₂ catalyzed two-component [5+2+1] cycloaddition of ene-vinylcyclopropanes and CO for the synthesis of fused bicyclic cyclooctenones has been designed and experimentally realized. The key point behind this design is to turn a disfavored reductive elimination of (sp³)C-Rh-C(sp³) to an easier migratory reductive elimination of (sp³)C-Rh-CO-C(sp³) by the introduction of CO. These reactions proceed in good yields for substrates with various tether types and substituents, providing a flexible, convenient, efficient, and stereocontrolled method for the construction of bicyclic cyclooctenones.