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 language | English (US) |
|---|---|
| Pages (from-to) | 39-41 |
| Number of pages | 3 |
| Journal | Synthesis |
| Issue number | 1 |
| DOIs | |
| State | Published - 1996 |
Keywords
- L-homoserine lactone
- L-α-vinylglycine
- enantiocontrolled synthesis
- phenylselenolate anion
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Cite this
Berkowitz, D. B., & Smith, M. K. (1996). A convenient synthesis of L-α-vinylglycine from L-homoserine lactone. Synthesis, (1), 39-41. https://doi.org/10.1055/s-1996-4177