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Synlett 1993; 1993(10): 731-732
DOI: 10.1055/s-1993-22587
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Asymmetric Synthesis of Allophenylnorstatine

Mark E. Bunnage* , Stephen G. Davies, Christopher J. Goodwin
  • *The Dyson Perrins Laboratory, South Parks Road, Oxford, OX1 3QY, UK.
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Publication Date:
19 March 2002 (online)

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Allophenylnorstatine [APNS; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid], a component of the HIV-1 protease inhibitor kynostatin, has been prepared via a tandem conjugate addition-electrophilic hydroxylation strategy using lithium (S)-(α-methylbenzyl)benzylamide and (+)- (camphorsulphonyl)oxaziridine. The effects of molecular recognition and enolate geometry on the selectivity of the reaction are discussed.