Palladium-Catalyzed Chemo- and Enantioselective C-O Bond Cleavage of α-Acyloxy Ketones by Hydrogenolysis

被引：38

作者：

Chen, Jianzhong ^{[1
]}

Zhang, Zhenfeng ^{[2
]}

Liu, Delong ^{[2
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Pharm, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 29期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

cleavage reactions; hydrogenolysis; ketones; kinetic resolution; palladium; ASYMMETRIC HYDROGENATION; PROTECTING GROUPS; PHENACYL ESTERS; DERIVATIVES; EFFICIENT; CYCLIZATION; PHOTOLYSIS; RESOLUTION; COMPLEXES; ALDEHYDES;

D O I：

10.1002/anie.201603590

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chemoselective C-O bond cleavage of the ester alkyl side-chain of alpha-acyloxy ketones was realized for the first time by a highly efficient palladium-catalyzed hydrogenolysis (S/C= 6000, the highest catalytic efficiency by far). Furthermore, a kinetic resolution of alpha-acyloxy ketones was first developed by enantioselective hydrogenolysis with good yields and up to 99% ee.

引用

页码：8444 / 8447

页数：4

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