title: Kinetic Resolution of β-Sulfonyl Ketones through Enantioselective β-Elimination using a Cation-Binding Polyether Catalyst.
abstract: Reported herein is the first enantioselective β-elimination reaction catalyzed by a chiral cation-binding polyether. By using this catalytic protocol, a wide range of β-sulfonyl ketones could be effectively resolved with high stereoselectivity (S up to >300). Key to the success of this process is the favorable secondary interactions of the catalyst with the Lewis basic groups on the sulfone substrate. The enone product of this process can be easily converted into the racemic starting material, and allows an effective recycling and overall synthesis of chiral β-sulfonyl ketones in high yield and excellent enantioselectivity.
authors.affiliation: Innovative Drug Research Centre, Chongqing University, Chongqing 401331 (China).
authors.forename: Liang
authors.initials: L
authors.lastname: Li
authors.affiliation: Innovative Drug Research Centre, Chongqing University, Chongqing 401331 (China).
authors.forename: Yidong
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Innovative Drug Research Centre, Chongqing University, Chongqing 401331 (China).
authors.forename: Yang
authors.initials: Y
authors.lastname: Peng
authors.affiliation: Innovative Drug Research Centre, Chongqing University, Chongqing 401331 (China).
authors.forename: Lei
authors.initials: L
authors.lastname: Yu
authors.affiliation: Innovative Drug Research Centre, Chongqing University, Chongqing 401331 (China).
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Wu
authors.affiliation: Innovative Drug Research Centre, Chongqing University, Chongqing 401331 (China). yhl198151@cqu.edu.cn.
authors.forename: Hailong
authors.initials: H
authors.lastname: Yan
keywords: asymmetric catalysis; ion pairs; kinetic resolution; organocatalysis; sulfones