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Issue 15, 2019
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Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst

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Abstract

The Ir-catalyzed highly efficient asymmetric hydrogenation of benzoxazinones and derivatives was successfully developed with N-methylated ZhaoPhos L5 as the ligand, which may display a new activation mode with a single anion-binding interaction among the substrate, cocatalyst Brønsted acid and ligand. This synthetic approach afforded a series of chiral dihydrobenzoxazinones and derivatives with excellent results (>99% conversion, 88–96% yields, 91–>99% ee, up to 40 500 TON). A key to success is the utilization of a strong Brønsted acid as the cocatalyst, such as hydrochloric acid, to form a possible single anion-binding interaction with the substrate and catalyst, which greatly contributed to the improvement of reactivity and enantioselectivity. Importantly, a creative and efficient synthetic route was developed to construct the important intermediate for the potential IgE/IgG receptor modulator through our catalytic methodology system.

Graphical abstract: Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst

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Publication details

The article was received on 28 Dec 2018, accepted on 03 Mar 2019 and first published on 19 Mar 2019


Article type: Edge Article
DOI: 10.1039/C8SC05797D
Chem. Sci., 2019,10, 4328-4333
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Highly efficient Ir-catalyzed asymmetric hydrogenation of benzoxazinones and derivatives with a Brønsted acid cocatalyst

    Z. Han, G. Liu, R. Wang, X. Dong and X. Zhang, Chem. Sci., 2019, 10, 4328
    DOI: 10.1039/C8SC05797D

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