Sequential One-Pot Synthesis of Dipeptides through the Transient Formation of CDI-N-Protected [alpha]-Aminoesters

The synthesis of dipeptides through a sequential one-pot procedure from commercially available protected amino acids is described. The transformation relies on the use of in situ generated transiently CDI-protected [alpha]-amino esters (CDI, e.g. N,N'-carbonyldiimidazole). In addition of being...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-06, Vol.359 (11), p.1963
Main Authors: deFigueiredo, Renata Marcia, Suppo, Jean-Simon, Midrier, Camille, Campagne, Jean-Marc
Format: Article
Language:English
Subjects:
Amino acids
Carbonyls
Cost engineering
Couplings
Esters
Synthesis
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Summary:The synthesis of dipeptides through a sequential one-pot procedure from commercially available protected amino acids is described. The transformation relies on the use of in situ generated transiently CDI-protected [alpha]-amino esters (CDI, e.g. N,N'-carbonyldiimidazole). In addition of being a highly atom-economical process, the couplings take place under very mild and neutral conditions without adding a base to the reaction medium. This protocol provides a concise and less costly route to dipeptide derivatives (12 examples, up to 87% yield) and is compatible with commonly used N-urethane protecting groups. Moreover, no epimerization was detected even when sensitive Boc-Cys(Bn)-OH was used.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700034