Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/73187
Título: | (3S,4R)-3,4-Dihydroxy-N-alkyl-l-homoprolines: synthesis and computational mechanistic studies |
Autor(es): | Freitas, David S. Sousa, Cristina E. A. Parente, Joana Drogalim, Artem Fortes, A. Gil Cerqueira, Nuno M. F. S. A. Rodríguez-Borges, José E. Alves, Maria José Chão |
Data: | 2019 |
Editora: | Royal Society of Chemistry |
Revista: | Organic & Biomolecular Chemistry |
Resumo(s): | This is the first synthetic report of (3S,4R)-dihydroxy-N-alkyl-l-homoprolines described so far. 2,4-O-Benzylidene-d-erythrose was obtained from d-glucose with an improved yield, and then transformed into the title (3S,4R)-dihydroxy-N-alkyl-l-homoprolines, in a two-step strategy, with excellent overall yields. Hydrogenolysis of the benzyl group led to the NH congener. The synthesis of final products from 1,4-lactone intermediates was studied by computational means either under acidic or basic conditions. The theoretical mechanism studies fully explain the experimental results: (a) an equilibrium between l-homoprolines and their bicyclic counterparts is established in acids; (b) the equilibrium suffers a complete displacement towards the l-homoproline side in a basic medium. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/73187 |
DOI: | 10.1039/C9OB02141H |
ISSN: | 1477-0520 |
Versão da editora: | https://pubs.rsc.org/en/content/articlelanding/2019/ob/c9ob02141h#!divAbstract |
Arbitragem científica: | yes |
Acesso: | Acesso restrito UMinho |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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Synthesis-2019.pdf Acesso restrito! | Accepted Manuscript | 1,81 MB | Adobe PDF | Ver/Abrir |
Este trabalho está licenciado sob uma Licença Creative Commons