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 language | English (US) |
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Pages (from-to) | 3102-3109 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 65 |
Issue number | 16 |
DOIs | |
State | Published - Apr 18 2009 |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry