title: Highly efficient asymmetric hydrogenation of cyano-substituted acrylate esters for synthesis of chiral γ-lactams and amino acids.
abstract: A highly efficient and enantioselective synthesis of γ-lactams and γ-amino acids by Rh-catalyzed asymmetric hydrogenation has been developed. Using the Rh-(S,S)-f-spiroPhos complex, under mild conditions a wide range of 3-cyano acrylate esters including both E and Z-isomers and β-cyano-α-aryl-α,β-unsaturated ketones were first hydrogenated with excellent enantioselectivities (up to 98% ee) and high turnover numbers (TON up to 10,000).
authors.affiliation: Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, No. 19 Xinjiekouwai St., Beijing 100875, China. ghhou@bnu.edu.cn.
authors.forename: Duanyang
authors.initials: D
authors.lastname: Kong
authors.forename: Meina
authors.initials: M
authors.lastname: Li
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
authors.forename: Guofu
authors.initials: G
authors.lastname: Zi
authors.forename: Guohua
authors.initials: G
authors.lastname: Hou
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D006865:Hydrogenation; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000179:Acrylates; D000596:Amino Acids; D004952:Esters; D007769:Lactams; D009570:Nitriles