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Directed Reductive Amination of β-Hydroxy-ketones: Convergent Assembly of the Ritonavir/Lopinavir Core

Dirk Menche,* Fatih Arikan, Jun Li and Sven Rudolph

*Helmholtz-Zentrum für Infektionsforschung GmbH, Medizinische Chemie, Mascheroder Weg 1, D-38124 Braunschweig, Germany, Email: dirk.menchehelmholtz-hzi.de

D. Menche, F. Arikan, J. Li, S. Rudolph, Org. Lett., 2007, 9, 267-270.

DOI: 10.1021/ol062715y (free Supporting Information)


Abstract

An efficient, directed reductive amination of β-hydroxy-ketones allows the stereoselective preparation of 1,3-syn-amino alcohols using Ti(iOPr)4 for coordination of the intermediate imino alcohol and PMHS as the reducing agent.

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proposed transition state



Key Words

reductive amination, 1,3-amino alcohols, polymethylhydrosiloxane


ID: J54-Y2007-0170