A convenient synthesis of L-α-vinylglycine from L-homoserine lactone

David B Berkowitz, Marianne K. Smith

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

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 (72%; ≥95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Boc) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.

Original languageEnglish (US)
Pages (from-to)39-41
Number of pages3
JournalSynthesis
Issue number1
StatePublished - Jan 1 1996

Fingerprint

Chromatography
Esters
Sodium
Acids
homoserine lactone
vinylglycine
sodium borohydride
diphenyldiselenide

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

A convenient synthesis of L-α-vinylglycine from L-homoserine lactone. / Berkowitz, David B; Smith, Marianne K.

In: Synthesis, No. 1, 01.01.1996, p. 39-41.

Research output: Contribution to journalArticle

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