title: Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes.
abstract: N-heterocyclic carbenes catalyze the oxidation of allylic, propargylic, and benzylic alcohols to esters with manganese(IV) oxide in excellent yields. A variety of ester derivatives can be synthesized, including protected carboxylates. This one-pot tandem oxidation represents the first organocatalytic oxidation of alcohols to esters. Saturated esters can also be accessed from aldehydes using this method. Through the utilization of a chiral catalyst, the acyl-heteroazolium intermediate becomes a chiral acylating agent, which can desymmetrize meso-1,2-diols. [reaction: see text].
authors.affiliation: Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
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
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D001592:Benzyl Alcohols / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D001592:Benzyl Alcohols; D004952:Esters; D006571:Heterocyclic Compounds; D006838:Hydrocarbons; C030011:carbene; D008697:Methane