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

Author(s)

dos Santos, Deborah A. ^{[1, 2]} ; da Silva, Allan R. ^{[1, 2]} ; Ellena, Javier ^[3] ; da Silva, Cecilia C. P. ^[1] ; Paixao, Marcio W. ^{[1, 2]} ; Correa, Arlene G. ^{[1, 2]}

Affiliation

^[1] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, BR-13565905 Sao Carlos, SP - Brazil

^[3] Univ Sao Paulo, Sao Carlos Inst Phys, BR-13560570 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: SYNTHESIS-STUTTGART; v. 52, n. 7, p. 1076-1086, APR 1 2020.
• Web of Science Citations: 0

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 alpha,beta-unsaturated aldehydes followed by the Passerini multicomponent reaction in an environmentally friendly solvent mixture (ethanol: water). (AU)

• FAPESP's process: 17/23867-0 - Organocatalyzed synthesis of aziridine aldehydes and applications in multicomponent reactions
• Grantee: Allan Ribeiro da Silva
• Support type: Scholarships in Brazil - Post-Doctorate
• FAPESP's process: 18/09961-7 - Molecular Design, Synthesis, and Trypanocidal Activity of Reversible Covalent Inhibitors of Cruzain Enzyme
• Grantee: Deborah Araujo dos Santos
• Support type: Scholarships in Brazil - Post-Doctorate
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support type: Research Grants - Research Centers in Engineering Program