N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters

被引：184
|
作者：
Maki, Brooks E. [1 ]
Scheidt, Karl A. [1 ]
机构：
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 19期
关键词：
D O I：
10.1021/ol8018488
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield. The reaction proceeds through a transient activated alcohol, which when generated in situ allows for the selective oxidation of the aldehyde under mild conditions. These conditions successfully oxidize potentially epimerizable aldehydes and alcohols while preserving stereochemical integrity. A variety of ester derivatives can be synthesized with variation of the acylated alcohol as well as the unactivated aldehyde.
引用
收藏
页码：4331 / 4334
页数：4
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