title: Enantioselective Rh-Catalyzed Carboacylation of C═N Bonds via C-C Activation of Benzocyclobutenones.
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.
authors.affiliation: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Lin
authors.initials: L
authors.lastname: Deng
authors.affiliation: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.|Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Xu
authors.forename: Hongbo
authors.initials: H
authors.lastname: Li
authors.affiliation: Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Guangbin
authors.initials: G
authors.lastname: Dong
mesh_terms: D002384:Catalysis; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003503:Cyclobutanes; C553737:cyclobutenone; D012238:Rhodium