title: Synthesis of chiral lactams via asymmetric hydrogenation of α,β-unsaturated nitriles.
abstract: A highly efficient Rh-catalyzed enantioselective hydrogenation of α,β-unsaturated nitriles containing ester/amide groups has been developed. Under mild conditions, with a complex of rhodium and (S,S)-f-spiroPhos as the catalyst, a variety of α,β-unsaturated nitriles bearing an ester or amide group were successfully hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.7% ee) and high turnover numbers (TON = 10 000). Furthermore, this catalyst system was also successfully applied to the synthesis of important chiral pharmacophore fragments, lactams, Paroxetine and amino acids.
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.affiliation: Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, No. 19 Xinjiekouwai St., Beijing 100875, China. ghhou@bnu.edu.cn.
authors.forename: Meina
authors.initials: M
authors.lastname: Li
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: Guofu
authors.initials: G
authors.lastname: Zi
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: Guohua
authors.initials: G
authors.lastname: Hou
mesh_terms: D006865:Hydrogenation; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*
chemical_list: D007769:Lactams; D009570:Nitriles