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

作者：Huang, Xiao-Fei; Zhang, Shao-Yun; Geng, Zhi-Cong; Kwok, Chun-Yuen; Liu, Peng; Li, Hai-Yan; Wang, Xing-Wang^*

来源：Advanced Synthesis & Catalysis, 2013, 355(14-15): 2860-2872.

DOI：10.1002/adsc.201300331

• asymmetric hydrogenation
• chiral diamine complexes
• -hydroxy sulfonamides
• -hydroxy sulfones
• phosphine-free

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.

• 出版日期2013-10-11
• 单位苏州大学