A Computationally Designed Rh(I)-Catalyzed Two-Component [5+2+1] Cycloaddition of Ene-vinylcyclopropanes and CO for the Synthesis of Cyclooctenones
Journal of the American Chemical Society2007Vol. 129(33), pp. 10060–10061
Citations Over TimeTop 10% of 2007 papers
Yuanyuan Wang, Jingxin Wang, Jiachun Su, Feng Huang, Lei Jiao, Yong Liang, Dazhi Yang, Shiwei Zhang, Paul A. Wender, Zhi‐Xiang Yu
Abstract
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.
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