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Synthesis 1996; 1996(1): 39-41
DOI: 10.1055/s-1996-4177
short paper
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A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone

David B. Berkowitz* , Marianne K. Smith
  • *Department of Chemistry, University of Nebraska-Lincoln, Lincoln Nebraska 68588-0304, USA, Fax +1(402)4729402; E-mail dbb@unlinfo.unl.edu
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Publication Date:
31 December 2000 (online)

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A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (71%; ≥ 95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Bod) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.

L-α-vinylglycine - L-homoserine lactone - phenylselenolate anion - enantiocontrolled synthesis

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