Journal of the Chemical Society. Perkin transactions I p. 2525 - 2532 (1994)
Update date:2022-07-30
Topics:
Hartzoulakis, Basil
Gani, David
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 additions occured with high diastereoselectivity.
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