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

Authors

David B. Berkowitz, University of Nebraska - LincolnFollow
Marianne K. Smith, University of Nebraska - Lincoln

Date of this Version

1996

Comments

Copyright Georg Thieme Verlag, Stuttgart.

Abstract

A procedure for the synthesis ofL-IX-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.