Journal of Organic Chemistry 2010-01-15

Asymmetric synthesis of the potent HIV-protease inhibitor, nelfinavir.

Sadagopan Raghavan, V Krishnaiah, B Sridhar

Index: J. Org. Chem. 75(2) , 498-501, (2010)

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Abstract

An asymmetric synthesis of nelfinavir is described starting from acrolein and (S)-methyl phenyl sulfoxide. The key features include (a) stereoselective preparation of a beta-protected amino-gamma,delta-unsaturated sulfoxide by the reaction of an alpha-sulfinyl carbanion with an unsaturated t-butyl sulfinylimine, (b) stereoselective bromohydrin formation using the pendant sulfoxide group as an intramolecular nucleophile, and (c) use of commercially or readily prepared inexpensive starting materials.