A hydrogen bond rationale for the enantioselective ß-alkenylboration of enones catalyzed by O-monoacyltartaric acids.
J Org Chem
; 79(14): 6754-8, 2014 Jul 18.
Article
em En
| MEDLINE
| ID: mdl-25001404
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 five-membered 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.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Tartaratos
/
Boranos
/
Cetonas
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
Argentina
País de publicação:
Estados Unidos