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:	RUIZ-BLANCO,YASSER B, ALVES,MARIA J, RODRÍGUEZ-BORGES,JOSÉ E, MOLINA,REINALDO
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2013
Materias:	Maximum hardness principle Minimum polarizability principle reactvity principles aromaticity of transition states 2H-azirine-3-carboxylate
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000400074
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spelling	oai:scielo:S0717-970720130004000742014-09-02STUDY 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-BUTADIENERUIZ-BLANCO,YASSER BALVES,MARIA JRODRÍGUEZ-BORGES,JOSÉ EMOLINA,REINALDO Maximum hardness principle Minimum polarizability principle reactvity principles aromaticity of transition states 2H-azirine-3-carboxylate 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.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.58 n.4 20132013-12-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000400074en10.4067/S0717-97072013000400074
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Maximum hardness principle Minimum polarizability principle reactvity principles aromaticity of transition states 2H-azirine-3-carboxylate
spellingShingle	Maximum hardness principle Minimum polarizability principle reactvity principles aromaticity of transition states 2H-azirine-3-carboxylate RUIZ-BLANCO,YASSER B ALVES,MARIA J RODRÍGUEZ-BORGES,JOSÉ E MOLINA,REINALDO 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
description	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.
author	RUIZ-BLANCO,YASSER B ALVES,MARIA J RODRÍGUEZ-BORGES,JOSÉ E MOLINA,REINALDO
author_facet	RUIZ-BLANCO,YASSER B ALVES,MARIA J RODRÍGUEZ-BORGES,JOSÉ E MOLINA,REINALDO
author_sort	RUIZ-BLANCO,YASSER B
title	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
title_short	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
title_full	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
title_fullStr	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
title_full_unstemmed	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
title_sort	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
publisher	Sociedad Chilena de Química
publishDate	2013
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000400074
work_keys_str_mv	AT ruizblancoyasserb studybasedonelectronicdescriptorsofthediastereoselectiveazadielsaldercycloadditionof1r10nndiethylsulfamoylisobornyl2hazirine3carboxylatetoee14diacetoxy13butadiene AT alvesmariaj studybasedonelectronicdescriptorsofthediastereoselectiveazadielsaldercycloadditionof1r10nndiethylsulfamoylisobornyl2hazirine3carboxylatetoee14diacetoxy13butadiene AT rodriguezborgesjosee studybasedonelectronicdescriptorsofthediastereoselectiveazadielsaldercycloadditionof1r10nndiethylsulfamoylisobornyl2hazirine3carboxylatetoee14diacetoxy13butadiene AT molinareinaldo studybasedonelectronicdescriptorsofthediastereoselectiveazadielsaldercycloadditionof1r10nndiethylsulfamoylisobornyl2hazirine3carboxylatetoee14diacetoxy13butadiene
_version_	1718445509481332736

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

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