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Kinetic Resolution of β‐Sulfonyl Ketones through Enantioselective β‐Elimination using a Cation‐Binding Polyether Catalyst
Author(s) -
Li Liang,
Liu Yidong,
Peng Yang,
Yu Lei,
Wu Xiaoyan,
Yan Hailong
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508127
Subject(s) - enantioselective synthesis , sulfonyl , kinetic resolution , chemistry , catalysis , stereoselectivity , sulfone , combinatorial chemistry , yield (engineering) , substrate (aquarium) , organic chemistry , lewis acids and bases , materials science , alkyl , oceanography , geology , metallurgy
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.