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Issue 9, 2017
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Nickel-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins: an efficient approach to chiral amines

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Abstract

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

Graphical abstract: Nickel-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins: an efficient approach to chiral amines

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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., 2017,8, 6419-6422
  • Open access: Creative Commons BY license
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    Nickel-catalyzed asymmetric hydrogenation of β-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, 8, 6419
    DOI: 10.1039/C7SC02669B

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