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

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...

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Veröffentlicht in:Journal of the American Chemical Society 2007-08, Vol.129 (33), p.10060-10061
Hauptverfasser: Wang, Yuanyuan, Wang, Jingxin, Su, Jiachun, Huang, Feng, Jiao, Lei, Liang, Yong, Yang, Dazhi, Zhang, Shiwei, Wender, Paul A, Yu, Zhi-Xiang
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Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja072505w