Artículo
A Hydrogen Bond Rationale for the Enantioselective beta-Alkenylboration of Enones Catalyzed by O-Monoacyltartaric Acids
Fecha de publicación:
06/2014
Editorial:
American Chemical Society
Revista:
Journal of Organic Chemistry
ISSN:
0022-3263
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
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.
Palabras clave:
Asymmetric Conjugate Alkenylboration
,
Organocatalysis
,
Dft Calculations
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Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Articulos de INST.DE QUIMICA ROSARIO
Citación
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
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