Asymmetric Synthesis of α-Methylglutamic Acid and α-Methylornithine by a Chiral Isocyano Amide Reagent
- 1 June 1985
- journal article
- research article
- Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry
- Vol. 49 (6) , 1761-1765
- https://doi.org/10.1080/00021369.1985.10866952
Abstract
An efficient approach to the asymmetric syntheses of α-methylglutamic acid and α-methylornithine is described. Two chiral reagents, (2′S)-N-(2′-methoxymethylpyrrolidine)-2-isocyanopropionamide 4 and (2′S)-N-(2′-hydroxymethylpyrrolidine)-2-isocyanopropionamide 5, were employed for the asymmetric induction. α-Methylglutamic acid 7 was synthesized by the asymmetric Michael-addition of methyl acrylate to 4 and 5 as the key step. The optical yield of 7 was 10~45% (R-form). α-Methylornithine 12 was also synthesized by the reaction of 4 with acrylonitrile as the key step. The optical yield of 12 was 31.7% (R-form).This publication has 4 references indexed in Scilit:
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