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Preparation of enantiomerically pure derivatives of 3 amino butanoic and 3 mercaptobutanoic acid by s n 2 ring opening of the beta lactone and a 1 3 dioxanone derived from 3 hydroxybutanoic acid


, : Preparation of enantiomerically pure derivatives of 3 amino butanoic and 3 mercaptobutanoic acid by s n 2 ring opening of the beta lactone and a 1 3 dioxanone derived from 3 hydroxybutanoic acid. Helvetica Chimica Acta 70(5): 1326-1332

From (S)-4-methyloxetan-2-one (1), the .beta.-butyrolactone readily available from the biopolymer (R)-polyhydroxybutyrate (PHB) and various C, N, O and S nucleophiles, the following compounds are prepared: (S)-2-hydroxy-4-octanone (3), (R)-3-aminobutanoic acid (7) and its N-benzyl derivative 5, (R)-3-azidobutanoic acid (6), (R)-3-mercaptobutanoic acid (10), (R)-3-(phenylthio)butanoic acid (8) and its sulfoxide 9. The (6R)-2,6-dimethyl-2-ethoxy-1,3-dioxan-4-one (4) from (R)-3-hydroxybutanoic acid undergoes SN2 ring opening with benzylamine to give the N-benzyl derivative (ent-5-) of (S)-3-aminobutanoic acid in 30-40% yield.

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