@article{f12d0a3ec8e64d4e93487af7e9f4f1a3,
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.",
author = "Maki, {Brooks E.} and Audrey Chan and Phillips, {Eric M.} and Scheidt, {Karl A.}",
note = "Funding Information: Financial support was provided by NIH/NIGMS (GM73072), Northwestern University, the PRF (Type-G), Abbott Laboratories, Amgen, AstraZeneca, 3M, GlaxoSmithKline, the Sloan Foundation, and Boerhinger-Ingelheim (New Investigator Awards). B.E.M. was supported by a GAANN Fellowship. A.C. is the recipient of a Dow Chemical Company Fellowship. E.M.P. is the recipient of an American Chemistry Society Division of Organic Chemistry Graduate Fellowship sponsored by Organic Reactions (2008–2009). We thank FMCLithium, Sigma–Aldrich, and BASF for providing reagents used in this research. Funding for the NU Integrated Molecular Structure Education and Research Center (IMSERC) has been furnished in part by the NSF (CHE-9871268). The authors wish to thank John M. Roberts for assistance in the synthesis of triazolium salt H .",
year = "2009",
month = apr,
day = "18",
doi = "10.1016/j.tet.2008.10.033",
language = "English (US)",
volume = "65",
pages = "3102--3109",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "16",
}