re- andsi-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt: A Highly Stereoselective Synthesis of the HIV Protease Inhibitor Amprenavir (Vertex 478)
- 12 July 1999
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 38 (13-14) , 1931-1934
- https://doi.org/10.1002/(sici)1521-3773(19990712)38:13/14<1931::aid-anie1931>3.0.co;2-4
Abstract
Either amprenavir (1) or its C(2) diastereomer can be synthesized in a simple way by the use of a nitroaldol reaction carried out in the presence of one or the other of the two ammonium ions 2. The 1,3‐diamino‐2‐hydroxypropyl structural element of 1 is also found in many other peptidomimetics and HIV protease inhibitors. Described here is a new strategy for possible application to direct and stereocontrolled synthesis of such compounds.This publication has 0 references indexed in Scilit: