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Short Paper | Regular issue | Vol 100, No. 2, 2020, pp.241-252
Published online, 12th February, 2020
DOI: 10.3987/COM-19-14173
A Facile Synthesis of 4-Substituted Glutamate Derivative via 1,3-Dipolar Cycloaddition of Dimethyl 2- Methyleneglutarate and Nitrone Derived (-)-Menthone

Abigail Kempf, Jaffarguriqbal Singh, Dina C. Merrer, and Richard Washington Denton*

*Chemistry And Environmental Science, Medgar Evers College- CUNY, 142- Home Street, Valley Stream, NY 11580


The 1,3-dipolar cycloaddition reaction of dimethyl 2-methyleneglutarate and (-)-menthone-derived nitrone occurred with moderate selectively to produce the desired isoxazolidine which was a direct precursor to the (2S,4S)-substituted glutamate derivative in an overall yield of 20%. The possibility of preparing the unnatural amino acid, (S)-(+)-lycoperdic acid was studied based on its evidence within the mass spectra of the final product.