Sequential One‐Pot Synthesis of Dipeptides through the Transient Formation of CDI‐N‐Protected α‐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 α‐amino esters (CDI, e.g. N,N′‐carbonyldiimidazole). In addition of being a highly at...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-06, Vol.359 (11), p.1963-1968
Main Authors: de Figueiredo, Renata Marcia, Suppo, Jean‐Simon, Midrier, Camille, Campagne, Jean‐Marc
Format: Article
Language:English
Subjects:
amide bond formation
atom economy
base-free procedure
dipeptides
non-activated carboxylic acids
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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 α‐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