Lin Deng1, Tao Xu1,2, Hongbo Li, Guangbin Dong1. 1. Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States. 2. Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, China.
Abstract
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.
Herein we describe the first enantioselective Rh-catalyzed carboacylation of n class="Chemical">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.
Authors: C Altomare; S Cellamare; A Carotti; G Casini; M Ferappi; E Gavuzzo; F Mazza; P T Carrupt; P Gaillard; B Testa Journal: J Med Chem Date: 1995-01-06 Impact factor: 7.446
Authors: Kuo Zhao; Kenji Yamashita; Joseph E Carpenter; Trevor C Sherwood; William R Ewing; Peter T W Cheng; Robert R Knowles Journal: J Am Chem Soc Date: 2019-05-23 Impact factor: 15.419