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
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-diyldia...
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| Autores principales: | , , , |
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| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
2013
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| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000400074 |
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| Sumario: | 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. |
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