Asymmetric Hydrogenation of β-Keto Sulfonamides and β-Keto Sulfones with a Chiral Cationic Ruthenium Diamine Catalyst

被引：30

作者：

Huang, Xiao-Fei ^{[1
]}

Zhang, Shao-Yun ^{[1
]}

Geng, Zhi-Cong ^{[1
]}

Kwok, Chun-Yuen ^{[1
]}

Liu, Peng ^{[1
]}

Li, Hai-Yan ^{[1
]}

Wang, Xing-Wang ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 14-15期

基金：

中国国家自然科学基金;

关键词：

asymmetric hydrogenation; chiral diamine complexes; -hydroxy sulfonamides; -hydroxy sulfones; phosphine-free; HIGHLY ENANTIOSELECTIVE HYDROGENATION; STEREOSELECTIVE-SYNTHESIS; IRIDIUM CATALYSTS; MECHANISM; QUINOLINES; ACID; DERIVATIVES; PRECURSORS; CARBANIONS; COMPLEXES;

D O I：

10.1002/adsc.201300331

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Optically active -hydroxy sulfonamides and -hydroxy sulfones are very important building blocks for the preparation of bioactive compounds and pharmaceuticals. In this work, a highly efficient asymmetric hydrogenation of -keto sulfonamides and -keto sulfones has been developed using the phosphine-free chiral ruthenium complex Ru(OTf)(TsDPEN)((6)-p-cymene) as the catalyst, to afford the corresponding -hydroxy sulfonamides and -hydroxy sulfones in high yields with excellent optical purities. In addition, a cascade asymmetric hydrogenation/dynamic kinetic resolution (DKR) of racemic cyclic -keto sulfonamides and -keto sulfones was also realized using the same catalyst, to give the corresponding chiral cyclic -hydroxy sulfonamides and -hydroxy sulfones in good yields with excellent enantio- and diastereoselectivities.

引用

页码：2860 / 2872

页数：13

共 83 条

[1] Mechanism of the hydrogenation of ketones catalyzed by trans-dihydrido(diamine)ruthenium(II) complexes [J].