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Amino acids

(S)-alpha-methyl,alpha-amino acids: a new stereocontrolled synthesis.


PMID 19363669

Abstract

A new and convenient stereocontrolled synthesis of the optically pure (S)-alpha-methyl,alpha-amino acids 6(a-d) that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione (1) is described. The (S)-1-phenylethyl group, bonded to each of the N-atoms of the 2,5-diketopiperazine, acts as a chiral inductor in the first alkylation, while the steric hindrance appears to be the determining factor of stereocontrol in third and forth alkylation.

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