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. 1996 Jan;1996(1):39-41.
doi: 10.1055/s-1996-4177.

A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone

David B Berkowitz  1 , Marianne K Smith  1
Affiliations

A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone

David B Berkowitz et al. Synthesis (Stuttg). 1996 Jan.

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% yield; ≥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.

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