An expeditious asymmetric synthesis of allophenylnorstatine

Article abstract of DOI:10.1016/S0040-4020(01)89672-1

Allophenylnorstatine [APNS; (2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid], a novel amino acid found in the kynostatin class of HIV-I protease inhibitors, has been prepared in 39% overall yield via a tandem conjugate addition-electrophilic hydroxylation protocol using lithium (S)-(α-methylbenzyl)benzylamide and (+)-(camphorsulfonyl)oxaziridine. An unprecedented level of molecular recognition between a homochiral β-amino enolate and a homochiral oxaziridine is identified and the importance of enolate geometry upon hydroxylation stereoselectivity is also addressed.