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2005
Peptides
U 0400
11- 195
Study of the Effect of the Nature of the Side Chain in Esters of α-Amino Acids on
the Diastereoselectivity of Condensation with 5(4H)-Oxazolone in the Synthesis of
Dipeptides with N-Terminal N-Acetylphenylalanine. — The formation of dipeptides, e.g. (III), via intermediate oxazolones is accompanied by racemization.
(S)-Oxazolones react more slowly and are converted to the (R)-enantiomers. As a result
of this dynamic kinetic resolution the (R,S)-diastereomers (III) are predominantly
formed. More complex side-chains in compounds (III) increase diastereoselectivity.
— (KRASNOV, V. P.; ZHDANOVA*, E. A.; SOLIEVA, N. Z.; SADRETDINOVA, L.
S.; BUKRINA, I. M.; DEMIN, A. M.; LEVIT, G. L.; EZHIKOVA, M. A.; KODESS,
M. I.; Russ. Chem. Bull. 53 (2004) 6, 1331-1334; Inst. Org. Synth., Ural Div. Russ.
Acad. Sci., Ekaterinburg 620219, Russia; Eng.) — C. Oppel
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