Efficient Enrichment of Chiral β-Sulfonyl Ketones through Asymmetric β-Elimination

Yidong Liu; Wenling Qin; Hailong Yan

doi:10.1055/s-0036-1588632

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(20): 2756-2760
DOI: 10.1055/s-0036-1588632

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Efficient Enrichment of Chiral β-Sulfonyl Ketones through Asymmetric β-Elimination

Yidong Liu

Innovative Drug Research Centre, Chongqing University, Chongqing 401331, P. R. of China eMail: yhl198151@cqu.edu.cn

,

Wenling Qin

Innovative Drug Research Centre, Chongqing University, Chongqing 401331, P. R. of China eMail: yhl198151@cqu.edu.cn

,

Hailong Yan*

Innovative Drug Research Centre, Chongqing University, Chongqing 401331, P. R. of China eMail: yhl198151@cqu.edu.cn

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Abstract

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Abstract

Chiral sulfones are important functionalities of various interesting organic compounds. Herein we reported a catalytic enantioselective β-elimination reaction for the first time and realized the kinetic resolution of racemic β-sulfonyl ketones. The resulted enones could be recovered to re-perform the catalytic resolution. This protocol overcame the yield limitation of 50% of resolution procedures. The resulting chiral β-sulfonyl ketones were successfully transformed into corresponding amide, hydrazine, and alcohols with good stereocontrol, demonstrating the application prospect of this reaction system.

Key words

enantioselective β-elimination - chiral sulfone - kinetic resolution

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