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

被引：34
|
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
收藏
页码：8444 / 8447
页数：4
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