Issue 18, 1994
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid

Basil Hartzoulakis  and  David Gani  

Abstract

Arndt–Eistert homologation of suitably protected (2S, 3S)-3-methylaspartic acid occurs with retention of configuration at C-3 to give, ultimately, (2S, 3R)-3-methylglutamic acid. (2S, 3R)-3-Methylglutamic acid was also prepared in good yield via the conjugate addition of the lithiated anion of the bis-lactim ether of cyclo-(R-Val -Gly) to methyl (E)-butenoate. The analogous reaction performed using isopentyl (Z)-butenoate ultimately gave (2S, 3S)-3-methylglutamic acid. Both conjugate addition occurs with high diastereoselectivity.

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Article information

DOI
https://doi.org/10.1039/P19940002525
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 2525-2531

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Syntheses of (2S,3R)- and (2S,3S)-3-methylglutamic acid

B. Hartzoulakis and D. Gani, J. Chem. Soc., Perkin Trans. 1, 1994, 2525 DOI: 10.1039/P19940002525

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