title: Highly enantioselective arylation of N-tosylalkylaldimines catalyzed by rhodium-diene complexes.
abstract: A highly enantioselective rhodium-catalyzed arylation of aliphatic N-tosylaldimines has been developed. The combination of chiral bicyclo[3.3.0]octadiene ligands, an active rhodium hydroxide complex, and neutral reaction conditions is the key to achieving high yield and enantioselectivity. The application of this method is demonstrated by the enantioselective synthesis of chiral 2-aryl pyrrolidines and piperidines in a one-pot procedure. Furthermore, excellent results are also obtained for the imine substrates with the more readily cleavable N-nosyl protecting group.
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Cui
authors.forename: Hong-Jie
authors.initials: HJ
authors.lastname: Yu
authors.forename: Rui-Feng
authors.initials: RF
authors.lastname: Yang
authors.forename: Wen-Yun
authors.initials: WY
authors.lastname: Gao
authors.forename: Chen-Guo
authors.initials: CG
authors.lastname: Feng
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007097:Imines; D010880:Piperidines; D011759:Pyrrolidines; D012238:Rhodium