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Letter

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

Supporting Info

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

Gesellschaft fr Biotechnologische Forschung mbH (recently renamed to Helmholtz-Zentrum fr Infektionsforschung GmbH), Medizinische Chemie, Mascheroder Weg 1, D-38124 Braunschweig, Germany

Org. Lett., 2007, 9 (2), pp 267–270

DOI: 10.1021/ol062715y

Publication Date (Web): December 23, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, dirk.menche@helmholtz-hzi.de

Abstract

An efficient procedure for the directed reductive amination of β-hydroxy-ketones (3) for the stereoselective preparation of 1,3-syn-amino alcohols (6) is reported. The operationally simple protocol uses Ti(ⁱOPr)₄ for coordination of the intermediate imino alcohol (5) and PMHS as the reducing agent. The method was expanded to an asymmetric aldol reductive amination sequence to allow a highly convergent synthesis of the hydroxy-amine core of the HIV-protease inhibitors ritonavir and lopinavir.

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Published In Issue January 18, 2007
Received November 7, 2006

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Letter

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