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Synthesis of chiral 1,3-bis(1-(diarylphosphoryl)ethyl)-benzenes via Ir-catalyzed double asymmetric hydrogenation of bis(diarylvinylphosphine oxides)

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Abstract

A class of chiral 1,3-bis(diarylphosphinoethyl)benzenes, which are key intermediates for the synthesis of PCP-type chiral pincer ligands, were prepared in high diastereomeric ratios and excellent ee values via double asymmetric hydrogenation of the corresponding bis(diarylvinylphosphine oxide) substrates using a SpinPhox/Ir(I) complex as the catalyst. The hydrogenation product 5a was readily transformed into the corresponding borane-protected chiral PCP-type pincer ligand 7a with high enantiomeric excess, exemplifying a viable synthetic route to optically active chiral PCP pincer ligands.

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Authors and Affiliations

  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Xu Liu, ZhaoBin Han, Zheng Wang & KuiLing Ding

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  1. Xu Liu
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  2. ZhaoBin Han
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  3. Zheng Wang
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  4. KuiLing Ding
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Correspondence to KuiLing Ding.

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Dedicated to Professor Qian Changtao on the occasion of his 80th birthday.

DING KuiLing was born in Henan Province (China) in 1966. He received his B.Sc. degree from Zhengzhou University in 1985 and Ph.D. degree from Nanjing University in 1990 under the supervision of professor Yangjie Wu. He became an assistant professor at Zhengzhou University in 1990 and full professor at the same place in 1995. During 1993–1994 he was engaged in postdoctoral research with professor Teruo Matsuura at Ryukoku University (Japan). In the period from 1997 to 1998 he was a UNESCO research fellow with Professor Koichi Mikami at Tokyo Institute of Technology (Japan). He joined the Shanghai Institute of Organic Chemistry in 1999, where he is currently a professor of chemistry. His research interests include development of new chiral catalysts and methodologies for asymmetric catalysis.

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Liu, X., Han, Z., Wang, Z. et al. Synthesis of chiral 1,3-bis(1-(diarylphosphoryl)ethyl)-benzenes via Ir-catalyzed double asymmetric hydrogenation of bis(diarylvinylphosphine oxides). Sci. China Chem. 57, 1073–1078 (2014). https://doi.org/10.1007/s11426-014-5134-7

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  • DOI: https://doi.org/10.1007/s11426-014-5134-7

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