Synlett 2016; 27(20): 2756-2760
DOI: 10.1055/s-0036-1588632
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© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 24 August 2016

Accepted after revision: 30 September 2016

Publication Date:
20 October 2016 (online)

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.

 
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