Organic Chemistry Portal

Abstracts

Search:

Highly Enantioselective One-Pot Synthesis of Chiral β-Hydroxy Sulfones via Asymmetric Transfer Hydrogenation in an Aqueous Medium

Dacheng Zhang, Tanyu Cheng*, Qiankun Zhao, Jianyou Xu and Guohua Liu*

*Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234, P. R. China, Email: tychengshnu.edu.cn, ghliushnu.edu.cn

D. Zhang, T. Cheng, Q. Zhao, J. Xu, G. Liu, Org. Lett., 2014, 16, 5764-5767.

DOI: 10.1021/ol502832a (free Supporting Information)


Abstract

In a one-pot synthesis of optically active β-hydroxy sulfones, intermediate β-keto sulfones obtained via a nucleophilic substitution reaction of α-bromoketones and sodium sulfinates were reduced through Ru-catalyzed asymmetric transfer hydrogenation using HCOONa as a hydrogen source. This mild transformation in an aqueous medium provides chiral β-hydroxy sulfones with high yields and excellent enantioselectivities.

see article for more examples



Key Words

sulfones, formate


ID: J54-Y2014