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Synthesis 2020; 52(07): 1076-1086
DOI: 10.1055/s-0039-1690774
DOI: 10.1055/s-0039-1690774
paper
Green One-Pot Asymmetric Synthesis of Peptidomimetics via Sequential Organocatalyzed Aziridination and Passerini Multicomponent Reaction
The authors gratefully acknowledge Fundação de Amparo à Pesquisa do Estado de São Paulo (grants 2013/07600-3, 2014/50249-8, 2017/23867-0 and 2018/09961-7), GlaxoSmithKline, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (Finance Code 001), and Conselho Nacional de Desenvolvimento Científico e Tecnológico (grants 302634/2016-9, 305190/2017-2 and 429748/2018-3) for funding and fellowships.Further Information
Publication History
Received: 05 November 2019
Accepted after revision: 01 December 2019
Publication Date:
16 December 2019 (online)
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).
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690774.
- Supporting Information
- CIF File
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