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A mechanochemical approach to access the proline–proline diketopiperazine framework

Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline–proline dipeptides under solvent-free conditions. A deprotection–cycl...

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Detalles Bibliográficos
Autores principales: Pétry, Nicolas, Benakki, Hafid, Clot, Eric, Retailleau, Pascal, Guenoun, Farhate, Asserar, Fatima, Sekkat, Chakib, Métro, Thomas-Xavier, Martinez, Jean, Lamaty, Frédéric
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5669228/
https://www.ncbi.nlm.nih.gov/pubmed/29114324
http://dx.doi.org/10.3762/bjoc.13.217
Descripción
Sumario:Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline–proline dipeptides under solvent-free conditions. A deprotection–cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro–Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.