re- and si-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt: A Highly Stereoselective Synthesis of the HIV Protease Inhibitor Amprenavir (Vertex 478)

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 HI...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 1999-07, Vol.38 (13-14), p.1931-1934
Main Authors: Corey, E. J., Zhang, Fu-Yao
Format: Article
Language:English
Subjects:
Amino alcohols
Chiral auxillaries
Diastereoselectivity
Nitroaldol reaction
Phase-transfer catalysis
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO;2-4