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DOI: 10.1055/s-2007-968324
Diastereoselective Reductive Amination of β-Hydroxyketones
D. Menche*, F. Arikan, J. Li, S. Rudolph
Helmholtz-Zentrum für Infektionsforschung GmbH, Braunschweig, Germany
Publication History
Publication Date:
23 March 2007 (online)
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Significance
This article proposes an expedient way for preparing chiral 1,3-syn-amino alcohols from various enantiopure β-hydroxyketones by a Lewis acid promoted reductive amination. Hereby, Ti(Oi-Pr)4 assumes the role of the activating and directing metal species and polymethylhydrosiloxane (PHMS) serves as hydride donor. The ketones are converted with p-anisidine into the respective imine intermediates. Various chiral 1,3-syn-amino alcohols are thus obtained in good diastereomeric ratios ranging from 86:14 to 93:7. In order to underline the importance of this reaction in drug development, it was additionally applied to the preparation of a key intermediate in the syntheses of ritonavir and lopinavir, which are both known HIV-protease inhibitors.