Asymmetric hydrogenation of alpha-primary and secondary amino ketones: efficient asymmetric syntheses of (-)-arbutamine and (-)-denopamine |
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Authors: | Shang Gao Liu Duan Allen Scott E Yang Qin Zhang Xumu |
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Affiliation: | Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA. |
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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. |
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Keywords: | amino alcohols asymmetric catalysis enantioselectivity hydrogenation ketone |
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