Rhodium(II)/Chiral Phosphoric Acid-Cocatalyzed Enantioselective O-H Bond Insertion of α-Diazo Esters

被引：62
|
作者：
Zhang, Yiliang [1 ,2 ]
Yao, Yuan [1 ]
He, Li [1 ,2 ]
Liu, Yang [1 ]
Shi, Lei [1 ,2 ,3 ]
机构：
[1] Harbin Inst Technol, Sch Chem & Chem Engn, MIIT Key Lab Crit Mat Technol New Energy Convers, Harbin 150001, Heilongjiang, Peoples R China
[2] Harbin Inst Technol, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[3] Jingchu Univ Technol, Hubei Key Lab Drug Synth & Optimizat, Jingmen 448000, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 16期
关键词：
asymmetric catalysis; chiral phosphoric acids; alpha-diazo esters; reaction mechanism; rhodium; CARBENOID INSERTION; EFFICIENT APPROACH; ORGANIC-SYNTHESIS; COMPLEXES; DESIGN; WATER;
D O I：
10.1002/adsc.201700572
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A rhodium(II)/chiral phosphoric acid system has been developed for the asymmetric catalytic insertion of alpha-diazo esters into the O-H bond of carboxylic acids to generate an array of synthetically useful alpha-hydroxy ester derivatives in good ee (up to 95% ee). Furthermore, the substrate scope could be successfully extended to a range of phenols and alcohols with high yield (up to 92%) and excellent enantioselectivity (up to 97%) under mild reaction conditions. Additionally, a density functional theory (DFT) study was performed to elucidate the reaction mechanism.
引用
收藏
页码：2754 / 2761
页数：8
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