Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine.
[reaction: see text] Syntheses of variously modified ligands for the dinuclear zinc catalysts for the asymmetric aldol and nitroaldol (Henry) reactions are reported. Catalytic enantioselective nitroaldol reactions promoted by these modified ligands led to efficient syntheses of the beta-receptor agonists (-)-denopamine and (-)-arbutamine.
Trost
Barry M
BM
Department of Chemistry, Stanford University, California 94305-5080, USA. bmtrost@stanford.edu
Yeh
Vince S C
VS
Ito
Hisanako
H
Bremeyer
Nadine
N
D002395:Catecholamines / Q000138:chemical synthesis* / Q000378:metabolism; D004983:Ethanolamines / Q000138:chemical synthesis* / Q000378:metabolism; D008024:Ligands; D015032:Zinc / Q000378:metabolism*
D002395:Catecholamines; D004983:Ethanolamines; D008024:Ligands; C076559:arbutamine; D015032:Zinc; C037293:denopamine