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

页码：2754 / 2761

页数：8

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