Enantioselective Synthesis of Chiral Phosphonates via Rh/f-spiroPhos Catalyzed Asymmetric Hydrogenation of β,β-Disubstituted Unsaturated Phosphonates

The first asymmetric hydrogenation of β,β-diaryl unsaturated phosphonates has been realized for synthesis of β,β-diaryl chiral phosphonates with excellent enantioselectivities (up to 99.9% ee) catalyzed by the Rh-(R,R)-f-spiroPhos complex. Furthermore, this catalyst also exhibits comparably excellen...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-09, Vol.86 (17), p.12034-12045
Main Authors: Wang, Chaoqiong, Xie, Fang, Guo, Qianling, Xie, Chaochao, Zi, Guofu, Ye, Weiping, Zhou, Zhangtao, Hou, Guohua, Zhang, Zhanbin
Format: Article
Language:English
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Summary:The first asymmetric hydrogenation of β,β-diaryl unsaturated phosphonates has been realized for synthesis of β,β-diaryl chiral phosphonates with excellent enantioselectivities (up to 99.9% ee) catalyzed by the Rh-(R,R)-f-spiroPhos complex. Furthermore, this catalyst also exhibits comparably excellent performance for β-aryl-β-alkyl unsaturated phosphonates providing the corresponding chiral phosphonates with up to 99.9% ee values. This methodology provides a straightforward access to asymmetric synthesis of chiral phosphonates.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01397