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Synthesis 2011(17): 2796-2802  
DOI: 10.1055/s-0030-1260129
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Electronically Deficient Atropisomeric Bisphosphine Ligands and Their Application in Asymmetric Hydrogenation of Quinolines

De-Yang Zhanga,b, Duo-Sheng Wangb, Min-Can Wang*a, Chang-Bin Yub, Kai Gaob, Yong-Gui Zhou*b
a Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, P. R. of China
Fax: +86(371)67769024; e-Mail: wangmincan@zzu.edu.cn;
b State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, P. R. of China
Fax: +86(411)84379220; e-Mail: ygzhou@dicp.ac.cn;
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Publication History

Received 9 May 2011
Publication Date:
21 July 2011 (online)

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Abstract

A series of electronically deficient atropisomeric bisphos­phine ligands have been synthesized from (S)-MeO-BiPhep. The introduction­ of electron-withdrawing groups in the ligands had a dramatic influence on both the enantioselectivity and the activity of catalyst. The iridium complex of the MeO-BiPhep-based ligand bearing a trifluoromethanesulfonyl group was successfully applied in the asymmetric hydrogenation of quinolines with ee values of up to 95% and turnover numbers (TON) of up to 14,600.

Key words

iridium - asymmetric hydrogenation - electron-deficient ligands - quinolines

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