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Chemistry. 2007;13(27):7780-4.

Asymmetric hydrogenation of alpha-primary and secondary amino ketones: efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine.

Author information

1
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA.

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.

PMID:
17591728
DOI:
10.1002/chem.200700594
[Indexed for MEDLINE]

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