title: N-Heterocyclic Carbene-Catalyzed Oxidations.
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.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Rd., Evanston, Illinois, 60208.
authors.forename: Brooks E
authors.initials: BE
authors.lastname: Maki
authors.forename: Audrey
authors.initials: A
authors.lastname: Chan
authors.forename: Eric M
authors.initials: EM
authors.lastname: Phillips
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt