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)
摘要:
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.
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关键词:
Amino alcohols Chiral auxillaries Diastereoselectivity Nitroaldol reaction Phase‐transfer catalysis
DOI:
10.1002/(SICI)1521-3773(19990712)38:13/143.0.CO;2-4
被引量:
年份:
1999
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