N-Heterocyclic carbene-catalyzed oxidations

Brooks E. Maki, Audrey Chan, Eric M. Phillips, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

108 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)3102-3109
Number of pages8
JournalTetrahedron
Volume65
Issue number16
DOIs
StatePublished - Apr 18 2009

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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