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) |
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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