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https://hdl.handle.net/1822/63863
Título: | Study based on electronic descriptors of the diastereoselective aza-diels-alder cycloaddition of [(1r)-10-(n,n-diethylsulfamoyl)isobornyl] 2h-azirine-3-carboxylate to e,e-1,4-diacetoxy-1,3-butadiene |
Autor(es): | Ruiz-Blanco, Yasser B. Alves, Maria José Chão Rodríguez-Borges, José E. Molina, Reinaldo |
Palavras-chave: | Maximum hardness principle Minimum polarizability principle reactvity principles aromaticity of transition states 2H-azirine-3-carboxylate |
Data: | 2013 |
Editora: | Sociedad Chilena de Quimica |
Revista: | Journal of the Chilean Chemical Society |
Resumo(s): | Cycloaddition of chiral [(1R)-10-(N,N-diethylsulfamoyl)isobornyl] 2H-azirine-3-carboxylate to E,E-1,4-diacetoxy-1,3-butadiene shows complete diatereoselectivity giving a single cycloadduct (-)-(2S,5R,6R)-6-[(1R)-10-(N,N-diethylsulfamoyl)isobornyloxycarbonyl]-1-azabicyclo[4.1.0]hept-3-ene-2,5-diyldiacetate. Our main objective is to identify electronic/steric parameters capable of describing the observed tendencies of this reaction. The results of the calculations conclude that: even though the steric factors can play an important role at the initial steps of the reaction, at the transition states the behavior of several electronic parameters; like hardness, polarizability, aromaticity, charge transfer, etc is decisive enough to justify the obtained product. Finally, this work summarizes an exhaustive analysis of electronic descriptors and empirical reactivity principles, reaching a definitive and comprehensive explanation to the observed experimental result. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/63863 |
DOI: | 10.4067/S0717-97072013000400074 |
ISSN: | 0717-9324 |
e-ISSN: | 0717-9707 |
Versão da editora: | https://scielo.conicyt.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000400074&lng=en&nrm=iso&tlng=en |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |