Journal of the Chemical Society. Chemical communications p. 153 - 155 (1987)
Update date:2022-08-02
Topics:
Baldwin, Jack E.
Adlington, Robert M.
Robinson, Nicholas G.
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 ylidine 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.
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Doi:10.1139/v62-234
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(1987)Doi:10.1016/0022-328X(88)80069-X
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(2017)Doi:10.1016/j.tet.2008.11.083
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