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  • Title: A beta-lactone route to chiral gamma-substituted alpha-amino acids: application to the concise synthesis of (S)-alpha-azidobutyro lactone and a natural amino acid.
    Author: Tennyson RL, Cortez GS, Galicia HJ, Kreiman CR, Thompson CM, Romo D.
    Journal: Org Lett; 2002 Feb 21; 4(4):533-6. PubMed ID: 11843584.
    Abstract:
    [reaction: see text] Beta-lactones are useful synthetic intermediates allowing access to a number of functional arrays. In this report, enantiomerically pure 4-trichloromethyl-2-oxetanone is shown to be a versatile amino acid synthon leading to a variety of gamma-substituted alpha-amino acid precursors. The utility of this methodology was demonstrated by the concise synthesis of a protected homoserine equivalent, alpha-azidobutyro lactone, and a naturally occurring alpha-amino acid from the seeds of Blighia unijugata.
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