Asymmetric hydrogenation of alpha-primary and secondary amino ketones: efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine.
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.
Shang
Gao
G
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA.
Liu
Duan
D
Allen
Scott E
SE
Yang
Qin
Q
Zhang
Xumu
X
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
D000318:Adrenergic beta-Agonists; D002395:Catecholamines; D004983:Ethanolamines; D007659:Ketones; D006859:Hydrogen; C076559:arbutamine; C037293:denopamine