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dc.contributor.author
Grimblat, Nicolas  
dc.contributor.author
Sugiura, Masaharu  
dc.contributor.author
Pellegrinet, Silvina Carla  
dc.date.available
2016-06-06T21:17:44Z  
dc.date.issued
2014-06  
dc.identifier.citation
Grimblat, Nicolas; Sugiura, Masaharu; Pellegrinet, Silvina Carla; A Hydrogen Bond Rationale for the Enantioselective beta-Alkenylboration of Enones Catalyzed by O-Monoacyltartaric Acids; American Chemical Society; Journal of Organic Chemistry; 79; 14; 6-2014; 6754-6758  
dc.identifier.issn
0022-3263  
dc.identifier.uri
http://hdl.handle.net/11336/6071  
dc.description.abstract
DFT calculations suggest that O-monoacyl L-tartaric acids catalyze the asymmetric conjugate alkenylboration of enones through transition structures that are stabilized by hydrogen-bonding interactions. Formation of a fivemembered acyloxyborane is proposed. The hydrogen of the free carboxy group derived from the catalyst interacts with the carbonyl group of the cyclic acyloxyborane, stabilizing the transition structure and reducing the flexibility of the system. Additional stabilizing nonclassical CH···O hydrogen-bond interactions seem to determine the observed enantioselectivity.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
American Chemical Society  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
Asymmetric Conjugate Alkenylboration  
dc.subject
Organocatalysis  
dc.subject
Dft Calculations  
dc.subject.classification
Química Orgánica  
dc.subject.classification
Ciencias Químicas  
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS  
dc.title
A Hydrogen Bond Rationale for the Enantioselective beta-Alkenylboration of Enones Catalyzed by O-Monoacyltartaric Acids  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2016-06-01T13:36:43Z  
dc.journal.volume
79  
dc.journal.number
14  
dc.journal.pagination
6754-6758  
dc.journal.pais
Estados Unidos  
dc.journal.ciudad
Washington  
dc.description.fil
Fil: Grimblat, Nicolas. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina  
dc.description.fil
Fil: Sugiura, Masaharu. Kumamoto University. Graduate School of Pharmaceutical Sciences; Japón  
dc.description.fil
Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina  
dc.journal.title
Journal of Organic Chemistry  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/jo5012398  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/jo5012398  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/10.1021/jo5012398  

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