Journal of the Chemical Society. Perkin transactions I p. 537 - 540 (1996)
Update date:2022-08-11
Topics:
Elemes, Yiannis
Ragnarsson, Ulf
An alternative scheme for the synthesis of enantiopure α-deuteriated amino acids from a common intermediate is presented. Methyl bis(methylsulfanyl)methylene[2,2-2H2]glycinate was prepared in a mixture of MeOD and D2O with a catalytic amount of Na2CO3 and attached to (2R)-bornane-10,2-sultam. Alkylation of the corresponding enolate provided intermediates which after careful purification were first deprotected on nitrogen and then cleaved from the auxiliary to give deuteriated α-amino acids of very high purity (> 99% ee and > 98% D). These were directly converted into the corresponding Boc-L-[2-2H]-Ala, -Leu, -Phe and -(O-Bzl)Tyr derivatives, suitable for application in peptide synthesis. Boc-[2,2-2H2]Gly was also prepared.
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