N-Heterocyclic carbene-catalyzed oxidations

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

doi:10.1016/j.tet.2008.10.033

N-Heterocyclic carbene-catalyzed oxidations

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

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	3102-3109
Number of pages	8
Journal	Tetrahedron
Volume	65
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2008.10.033
State	Published - Apr 18 2009

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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AU - Chan, Audrey

AU - Phillips, Eric M.

AU - Scheidt, Karl A

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Y1 - 2009/4/18

N2 - 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.

AB - 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.

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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N-Heterocyclic carbene-catalyzed oxidations

Abstract

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