Published in
Royal Society of Chemistry, Chemical Communications, 23(50), p. 3100
DOI: 10.1039/c3cc49580a
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Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings .
Journal article published in 2014 by
Damien Beaufils,
Grégoire Danger,
Laurent Boiteau,
Jean-Christophe Rossi,
Robert Pascal 
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Abstract
A stereochemical study of a potentially prebiotic peptide-forming reaction was carried out as the first part of a systems chemistry investigation of potential paths for symmetry breaking. Substantial diastereomeric excesses result from a fast epimerization of the 5(4H)-oxazolone intermediate in aqueous solution.