Kinetic Resolution of β‐Sulfonyl Ketones through Enantioselective β‐Elimination using a Cation‐Binding Polyether Catalyst |
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| Authors: | Liang Li Yidong Liu Yang Peng Lei Yu Xiaoyan Wu Prof Hailong Yan |
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| Affiliation: | Innovative Drug Research Centre, Chongqing University, Chongqing 401331 (China) |
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| 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. |
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| Keywords: | asymmetric catalysis ion pairs kinetic resolution organocatalysis sulfones |
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