Mechanochemical Diastereoselective Substrate-Directed Synthesis of Pyrrole-Isoxazolidines via 1,3-Dipolar Cycloaddition of Maleimides with Nitrones
selectivity, and on the basis of this, empirical guidelines are presented for predicting the diastereoselectivity as a function of substituents in this cycloaddition. Furthermore, this mechanochemical approach provided a protocol with short reaction times and simple processing, eliminating the need for column chromatography purification. Scaling up to one product and detailed green metrics to all products indicated that this mechanochemical approach is a greener route in relation to the traditional solvent methods.
Authors
- Armando Ferrer (ORCID: https://orcid.org/0000-0002-6849-0232)
- Sílvio Cunha (ORCID: https://orcid.org/0000-0002-8822-517X)
- Iva S. de Jesus (ORCID: https://orcid.org/0000-0003-0254-3589)
- Anna Flávia da C. Lédo
- Mauro A. Bueno
Institutions
- Universidade Federal da Bahia (BR)
- Universidade Federal do Oeste da Bahia (BR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-07-27
- DOI
- https://doi.org/10.1021/acs.joc.6c00411
- Primary Topic
- Crystallography and molecular interactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Amparo à Pesquisa do Estado da Bahia