N-Heterocyclic Carbene-Catalyzed Oxidations.
Tetrahedron
; 65(16): 3102-3109, 2009 Apr 18.
Article
em En
| MEDLINE
| ID: mdl-20161230
ABSTRACT
N-Heterocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized, including protected carboxylates. The oxidation proceeds under mild conditions, with low loadings of a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Tetrahedron
Ano de publicação:
2009
Tipo de documento:
Article