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.

D. Balducci, I. Lazzari, M. Monari, F. Piccinelli, G. Porzi (2010). (S)-alpha-methyl-alpha-aminoacids : a new stereocontrolled synthesis. AMINO ACIDS, 38, 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.
2010
D. Balducci, I. Lazzari, M. Monari, F. Piccinelli, G. Porzi (2010). (S)-alpha-methyl-alpha-aminoacids : a new stereocontrolled synthesis. AMINO ACIDS, 38, 829-837 [10.1007/s00726-009-0289-9].
D. Balducci; I. Lazzari; M. Monari; F. Piccinelli; G. Porzi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/76845
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