Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes

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

doi:10.1021/ol062940f

Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes

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

244 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original language	English (US)
Pages (from-to)	371-374
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	2
DOIs	https://doi.org/10.1021/ol062940f
State	Published - Jan 18 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) 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.",

author = "Maki, {Brooks E.} and Audrey Chan and Phillips, {Eric M.} and Scheidt, {Karl A.}",

year = "2007",

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T1 - Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes

AU - Maki, Brooks E.

AU - Chan, Audrey

AU - Phillips, Eric M.

AU - Scheidt, Karl A.

PY - 2007/1/18

Y1 - 2007/1/18

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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.

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JO - Organic Letters

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ER -

Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes

Abstract

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