Green One-Pot Asymmetric Synthesis of Peptidomimetics via Sequential Organocatalyzed Aziridination and Passerini Multicomponent Reaction

Deborah A. dos Santos; Allan R. da Silva; Javier Ellena; Cecilia C. P. da Silva; Marcio W. Paixão; Arlene G. Corrêa

doi:10.1055/s-0039-1690774

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(07): 1076-1086
DOI: 10.1055/s-0039-1690774

paper

Green One-Pot Asymmetric Synthesis of Peptidomimetics via Sequential Organocatalyzed Aziridination and Passerini Multicomponent Reaction

Authors

Deborah A. dos Santos

^aCentre of Excellence for Research on Sustainable Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil eMail: agcorrea@ufscar.br

^bDepartment of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
Allan R. da Silva

^aCentre of Excellence for Research on Sustainable Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil eMail: agcorrea@ufscar.br

^bDepartment of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
Javier Ellena

^cSão Carlos Institute of Physics, University of São Paulo, 13560-570, São Carlos, SP, Brazil
Cecilia C. P. da Silva

^bDepartment of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
Marcio W. Paixão

^aCentre of Excellence for Research on Sustainable Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil eMail: agcorrea@ufscar.br

^bDepartment of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil
Arlene G. Corrêa ∗

^aCentre of Excellence for Research on Sustainable Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil eMail: agcorrea@ufscar.br

^bDepartment of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil

Abstract

Alle Artikel dieser Rubrik

Abstract

Peptidomimetics containing an aziridine moiety have been reported as potent cysteine protease inhibitors. In this sense, the development of stereoselective and sustainable synthetic strategies to obtain three-membered N-heterocyclic compounds has gained importance in the last decades. In this work, an efficient method was designed to achieve highly functionalized aziridine peptidomimetics via a sequential reaction, which involves the organocatalytic aziridination of α,β-unsaturated aldehydes followed by the Passerini multicomponent reaction in an environmentally friendly solvent mixture (ethanol: water).

Key words

peptidomimetics - green chemistry - organocatalysis - aziridine - multicomponent reaction

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Referenzen

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