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https://hdl.handle.net/1822/51343
Título: | Total facial selectivity of a D-erythrosyl aromatic imine in [4π + 2π] cycloadditions; synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines |
Autor(es): | Ferreira, Juliana Duarte, Vera C. M. Noro, Jennifer Martins Fortes, A. Gil Alves, Maria José Chão |
Data: | 1-Fev-2016 |
Editora: | Royal Society of Chemistry |
Revista: | Organic and Biomolecular Chemistry |
Citação: | Ferreira, J., Duarte, V. C., Noro, J., Fortes, A. G., & Alves, M. J. (2016). Total facial selectivity of ad-erythrosyl aromatic imine in [4π+ 2π] cycloadditions; synthesis of 2-alkylpolyol 1, 2, 3, 4-tetrahydroquinolines. Organic & biomolecular chemistry, 14(10), 2930-2937 |
Resumo(s): | Different electron-rich dienophiles were combined with the imine obtained from 2,4-O-benzylidene-D-erythrose and p-anisidine furnishing enantiomerically pure tetrahydroquinolines, by inverse electron-demand [4 pi + 2 pi] cycloaddition. The imine was also reacted with 2-substituted electron-rich 1,3-butadienes giving the diastereomeric pure product, resulting from the normal electron demand cycloaddition. The facial selectivity of both processes is proposed on the basis of a 1,4-relationship between the hydroxyl group and the nitrogen atom in the chiral N-(p-methoxyphenyl) imine derivative. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/51343 |
DOI: | 10.1039/c5ob02594j |
ISSN: | 1477-0520 |
Versão da editora: | http://pubs.rsc.org/-/content/articlehtml/2016/ob/c5ob02594j |
Arbitragem científica: | yes |
Acesso: | Acesso restrito autor |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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c5ob02594j.pdf Acesso restrito! | 415,15 kB | Adobe PDF | Ver/Abrir |