Enantioselective Rh-Catalyzed Carboacylation of C═N Bonds via C–C Activation of Benzocyclobutenones

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• 作者：Lin Deng ; Tao Xu ; Hongbo Li ; Guangbin Dong
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：January 13, 2016
• 年：2016
• 卷：138
• 期：1
• 页码：369-374
• 全文大小：596K
• ISSN：1520-5126

文摘

Herein we describe the first enantioselective Rh-catalyzed carboacylation of oximes (imines) via C–C activation. In this transformation, the benzocyclobutenone C1–C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh–C bonds add across a C═N bond, which provides a unique approach to access chiral lactams. A range of polycyclic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.