A new and convenient stereocontrolled synthesis of the optically pure (S)-alpha-methyl,alpha-aminoacids that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione 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.
(S)-alpha-methyl-alpha-aminoacids : a new stereocontrolled synthesis / D. Balducci; I. Lazzari; M. Monari; F. Piccinelli; G. Porzi. - In: AMINO ACIDS. - ISSN 0939-4451. - STAMPA. - 38:(2010), pp. 829-837. [10.1007/s00726-009-0289-9]
(S)-alpha-methyl-alpha-aminoacids : a new stereocontrolled synthesis
MONARI, MAGDA;PORZI, GIANNI
2010
Abstract
A new and convenient stereocontrolled synthesis of the optically pure (S)-alpha-methyl,alpha-aminoacids that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
