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A New Catalyst for the Asymmetric Henry Reaction: Synthesis of β-Nitroethanols in High Enantiomeric Excess

James D. White * and Subrata Shaw

*Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, United States, Email: James.whiteoregonstate.edu

J. D. White, S. Shaw, Org. Lett., 2012, 14, 6270-6273.

DOI: 10.1021/ol3030023 (free Supporting Information)


Abstract

A complex of copper(I) and a chiral tetrahydrosalen ligand was an efficient catalyst for the asymmetric Henry reaction, producing nitroaldol products in high yield and good stereoselectivity. Henry reactions catalyzed by this tetrahydrosalen-Cu(I) complex led to syntheses of β-adrenergic blocking agents (S)-toliprolol, (S)-moprolol, and (S)-propanolol.


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Key Words

Henry Reaction


ID: J54-Y2012-3910