title: Asymmetric hydrogenation of alpha-primary and secondary amino ketones: efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine.
abstract: Two beta-receptor agonists (-)-denopamine and (-)-arbutamine were prepared in good yields and enantioselectivities by asymmetric hydrogenation of unprotected amino ketones for the first time by using Rh catalysts bearing electron-donating phosphine ligands. A series of alpha-primary and secondary amino ketones were synthesized and hydrogenated to produce various 1,2-amino alcohols in good yields and with good enantioselectivies. This Rh electron-donating phosphine-catalyzed asymmetric hyderogenation represents one of the most promising and convenient approaches towards the asymmetric synthesis of chiral amino alcohols.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA.
authors.forename: Gao
authors.initials: G
authors.lastname: Shang
authors.forename: Duan
authors.initials: D
authors.lastname: Liu
authors.forename: Scott E
authors.initials: SE
authors.lastname: Allen
authors.forename: Qin
authors.initials: Q
authors.lastname: Yang
authors.forename: Xumu
authors.initials: X
authors.lastname: Zhang
mesh_terms: D000318:Adrenergic beta-Agonists / Q000138:chemical synthesis*; D002395:Catecholamines / Q000138:chemical synthesis*; D004983:Ethanolamines / Q000138:chemical synthesis*; D006859:Hydrogen / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000318:Adrenergic beta-Agonists; D002395:Catecholamines; D004983:Ethanolamines; D007659:Ketones; D006859:Hydrogen; C076559:arbutamine; C037293:denopamine