Your browser doesn't support javascript.
loading
Asymmetric conjugate addition of alkynylboronates to enones: rationale for the intriguing catalysis exerted by binaphthols.
Pellegrinet, Silvina C; Goodman, Jonathan M.
Afiliação
  • Pellegrinet SC; Instituto de Química Organica y de Síntesis (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario (2000), Argentina. spellegr@fbioyf.unr.edu.ar
J Am Chem Soc ; 128(10): 3116-7, 2006 Mar 15.
Article em En | MEDLINE | ID: mdl-16522071
The conjugate addition of alkynylboronates to enones catalyzed by binaphthols has been studied theoretically with DFT methods. The high reactivity of the alkynylboronate derived from binaphthol seems to arise from electronic effects since its acidic boron atom binds tightly to the enone carbonyl and lowers the activation energy of the alkynylboration step. Steric clashes between the atoms of the ligands on boron and the enone can be invoked to account for the observed facial diastereoselectivity. The competing hetero-Diels-Alder reactions are computed to be kinetically disfavored relative to alkynylborations.
Buscar no Google
Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Am Chem Soc Ano de publicação: 2006 Tipo de documento: Article País de afiliação: Argentina País de publicação: Estados Unidos
Buscar no Google
Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Am Chem Soc Ano de publicação: 2006 Tipo de documento: Article País de afiliação: Argentina País de publicação: Estados Unidos