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Nickel-catalyzed asymmetric hydrogenation of ?-acylamino nitroolefins: an efficient approach to chiral amines.

ABSTRACT: An efficient approach for synthesizing chiral ?-amino nitroalkanes has been developed via the Ni-catalyzed asymmetric hydrogenation of challenging ?-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 ?-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.

SUBMITTER: Gao W

PROVIDER: S-EPMC5632792 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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

Gao Wenchao W Lv Hui H Zhang Tonghuan T Yang Yuhong Y Chung Lung Wa LW Wu Yun-Dong YD Zhang Xumu X

Chemical science 20170704 9

An efficient approach for synthesizing chiral β-amino nitroalkanes has been developed <i>via</i> 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 mec ...[more]

PMID: 29163927

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