TEMP and copper cocatalyzed oxygenation of ketones with molecular oxygen: chemoselective synthesis of α-ketoesters

被引：41
作者：
Huang, Xiaoqiang [1 ]
Li, Xinwei [1 ]
Zou, Miancheng [1 ]
Pan, Jun [1 ]
Jiao, Ning [1 ,2 ]
机构：
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2015年 / 2卷 / 04期
基金：
中国国家自然科学基金;
关键词：
C BOND-CLEAVAGE; CATALYZED OXIDATION; AEROBIC OXIDATION; HYDROXY ESTERS; METHYL KETONES; ALCOHOLS; FUNCTIONALIZATION; ORGANOCATALYSIS; ESTERIFICATION; ACETOPHENONES;
D O I：
10.1039/c5qo00028a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and practical method for the synthesis of alpha-ketoesters through TEMP and copper cocatalyzed chemoselective oxidative coupling of commercially available methyl ketones with alcohols is developed. Mild conditions and broad substrate scope make this chemistry an efficient tool for the late-stage modification of bioactive compounds. Detailed mechanistic studies demonstrate a novel mechanism involving an organocatalytic cycle and SET process. The oxygenation process with molecular oxygen enables this transformation.
引用
收藏
页码：354 / 359
页数：6
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