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1. Stereoselective synthesis of N,N'-diaryl-2,5-dioxopiperazines from homochiral or racemic 2-bromopropananilides

Author

D'Angeli, Ferrucio, Marchetti, Paolo, Rondanin, Riccardo, and Bertolasi, Valerio

Subjects
Organic compounds -- Synthesis, Nitrogen compounds -- Research, Biological sciences, Chemistry
Abstract

The preparation and characterization of N,N'-diaryl-2,5-dioxopiperazines are described. The stereoselective synthesis involves the self-coupling of 2-bromopropananilides. The reaction can be controlled to favor cis-(R,R) or cis-(S,S)/trans-(R,S) isomers by starting either from a single enantiomer or racemate and by the promoter, aryl substituent and solvent. The six diastereomeric couples have been characterized by 1H NMR spectroscopy and X-ray crystallography.

Published
1996

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