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Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position

Abstract

With the assistance of hydrogen bonds, the first asymmetric hydrogenation of β cyanocinnamic esters has been developed, affording chiral β-cyano esters with excellent enantioselectivities (up to 99% ee). This novel methodology provides an efficient and concise synthetic route to chiral GABA-derivatives, such as (S)-Pregabalin, (R)-Phenibut, (R)-Baclofen. Interestingly, in this system, the catalyst with single H-bond donor performed better than that with double H-bond donors, which is a novel discovery in the metalorganocatalysis area.

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Publication details

The article was received on 26 Oct 2017, accepted on 02 Jan 2018 and first published on 04 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC04639A
Citation: Chem. Sci., 2018, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
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    Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position

    X. Li, C. You, Y. Yang, Y. Yang, P. Li, G. Gu, L. W. Chung, H. Lv and X. Zhang, Chem. Sci., 2018, Accepted Manuscript , DOI: 10.1039/C7SC04639A

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