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Asymmetric synthesis of unusual amino acids: Synthesis of optically pure isomers of β-methylphenylalanine

✍ Scribed by Ramalinga Dharanipragada; Ernesto Nicolas; Geza Toth; Victor J. Hruby

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 209 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93366-0

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✦ Synopsis

All the four individual isomers of R-methylphenylalanine have been synthesized in very high optical purities by utilizing in part the chiral imide enolate bromination methodology of Evans and co-workers.

Substitution of the diastereotopic X-hydrogens of many a-amino acids provides inprinciple, an approach to topographic control of peptide structure. Asymmetric synthesis of the desired amino acids is needed to facilitate these studies.

In this letter, we detail our approachi to the successful synthesis of all the four individual isomers of X-methylphenylalanine in very high optical purity.

In the recent years, several methods have been developedz*3 for the asymmetric synthesis of o-aminoacids. Among them, the elegant method of Evans and co-workers3

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