Asymmetric synthesis of the potent HIV-protease inhibitor, nelfinavir

Article abstract of DOI:10.1021/jo902048t

(Chemical Equation Presented) An asymmetric synthesis of nelfinavir is described starting from acrolein and (S)-methyl phenyl sulfoxide. The key features include (a) stereoselective preparation of a β-protected amino-γ,δ-unsaturated sulfoxide by the reaction of an α-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.