Selective reductions of cyclic 1,3-diesters using SmI(2) and H(2)O.
J Am Chem Soc
; 131(21): 7214-5, 2009 Jun 03.
Article
em En
| MEDLINE
| ID: mdl-19422232
ABSTRACT
SmI(2)-H(2)O reduces cyclic 1,3-diesters to 3-hydroxyacids with no over-reduction. Furthermore, the reagent system is selective for cyclic 1,3-diesters over acyclic 1,3-diesters and esters. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron transfer to the ester carbonyl and the anomeric stabilization of the resulting radical-anion intermediate. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Substâncias Redutoras
/
Ésteres
Idioma:
En
Ano de publicação:
2009
Tipo de documento:
Article