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Nickel-Catalyzed Asymmetric Hydrogenation of ß-Acylamino Nitroolefins: An Efficient Approach to Chiral Amines

Abstract

An efficient approach for synthesizing chiral β-amino nitroalkanes has been developed by Ni-catalyzed asymmetric hydrogenation of challenging β-amino nitroolefines under mild conditions, affording the desired products with excellent yields and high enantioselectivities. This protocol exhibited good compatibility of wide substrate scope and functional group. The synthesis of chiral β-amino nitroalkanes on gram scale has also been achieved. In addition, the reaction mechanism was elucidated by a combined experimental and computational study to involve acetate-assisted heterolytic H2 cleavage followed by 1,4-hydride addition to the nitroolefin and protonation

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Publication details

The article was received on 15 Jun 2017, accepted on 02 Jul 2017 and first published on 04 Jul 2017


Article type: Edge Article
DOI: 10.1039/C7SC02669B
Citation: Chem. Sci., 2017, Accepted Manuscript
  • Open access: Creative Commons BY license
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    Nickel-Catalyzed Asymmetric Hydrogenation of ß-Acylamino Nitroolefins: An Efficient Approach to Chiral Amines

    W. Gao, H. Lv, T. Zhang, Y. Yang, L. W. Chung, Y. Wu and X. Zhang, Chem. Sci., 2017, Accepted Manuscript , DOI: 10.1039/C7SC02669B

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