title: Highly regio- and enantioselective synthesis of γ,δ-unsaturated amido esters by catalytic hydrogenation of conjugated enamides.
abstract: An efficient and highly regio- and enantioselective catalytic asymmetric hydrogenation of α,γ-dienamido esters to γ,δ-unsaturated amido esters has been achieved using Rh/TangPhos as the catalyst. A series of γ,δ-unsaturated amido acids were furnished in excellent yields with up to 99% ee. This effective methodology was applied in the asymmetric synthesis of key intermediate of Ramipril, an ACE inhibitor.
authors.affiliation: Key Laboratory of Biomedical Polymers of Ministry of Education & College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072 (China).
authors.forename: Min
authors.initials: M
authors.lastname: Gao
authors.forename: Jing-jing
authors.initials: JJ
authors.lastname: Meng
authors.forename: Hui
authors.initials: H
authors.lastname: Lv
authors.forename: Xumu
authors.initials: X
authors.lastname: Zhang
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D006859:Hydrogen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D004952:Esters; D006859:Hydrogen
keywords: amino acids; asymmetric synthesis; hydrogenation; regioselectivity; rhodium