Nucleophilic ring opening of aziridine-2-carboxylates with Wittig reagents; an enantioefficient synthesis of unsaturated amino acids
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 3,p. 153-155
- https://doi.org/10.1039/c39870000153
Abstract
Reaction of N-tosyl- or N-acyl aziridine-(2S)-carboxylate esters with carbonyl stabilized Wittig reagents provides an isolable phosphorus ylide resulting from opening of the aziridine ring; this ylide reacts with carbonyl compounds to provide a novel synthesis of optically pure unsaturated amino acids, exemplified by enantioefficient syntheses of the naturally occuring (2S)-γ-methyleneglutamic acid and (E)-(2S)-4-ethylideneglutamic acid.Keywords
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