| Texto completo | |
| Autor(es): |
Ali, Sajjad
;
Milanezi, Henrique
;
Alves, Tania M. F.
;
Tormena, Claudio Francisco
;
Ferreira, Marco A. B.
Número total de Autores: 5
|
| Tipo de documento: | Artigo Científico |
| Fonte: | Journal of Organic Chemistry; v. 83, n. 15, p. 20-pg., 2018-08-03. |
| Resumo | |
A straightforward protocol integrating a sustainable approach for the synthesis of new 2,S-trans-THF nitrile derivatives enabling an easy diversification of its side chain scaffolds is described. The reaction tolerated different aromatic and alkyl substituents, affording the corresponding 2,5-trans-THFs in high diastereoselectivity. A detailed mechanistic study using DFT calculation reveals details of the ligand-exchange step, suggesting an inner-sphere syn attack to form the 2,5-trans stereochemistry as the most likely pathway, excluding the previous cation radical intermediate. The formation of a Co-C intermediate is suggested on the basis of the homolytic cleavage to give the previously proposed free carbon radical intermediate. (AU) | |
| Processo FAPESP: | 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock |
| Beneficiário: | Arlene Gonçalves Corrêa |
| Modalidade de apoio: | Auxílio à Pesquisa - Programa Centros de Pesquisa Aplicada |
| Processo FAPESP: | 13/02311-3 - Novas abordagens na síntese assimétrica de tetraidrofuranos e tetraidropiranos substituídos com potencial aplicação na preparação de moléculas bioativas |
| Beneficiário: | Marco Antonio Barbosa Ferreira |
| Modalidade de apoio: | Auxílio à Pesquisa - Regular |
| Processo FAPESP: | 15/08541-6 - Ressonância magnética nuclear: além da determinação estrutural |
| Beneficiário: | Claudio Francisco Tormena |
| Modalidade de apoio: | Auxílio à Pesquisa - Temático |