4.8 Article

Chiral-at-Metal Rh(III) Complex-Catalyzed Michael Addition of Pyrazolones with α,β-Unsaturated 2-Acyl Imidazoles

Journal

ORGANIC LETTERS
Volume 20, Issue 5, Pages 1312-1315

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00040

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Funding

  1. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  2. 100 Talents Programme of the Chinese Academy of Sciences

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An efficient enantioselective conjugate addition of pyrazolones with alpha,beta-unsaturated 2-aryl imidazoles catalyzed by chiral-at-metal rhodium complex is reported. The corresponding adducts were obtained in good yields (85%-96%) with excellent enantioselectivities (up to >99%). This protocol exhibits extraordinary reactivity, because of the fact that a complex with as little as 0.05 mol % Rh(III) can catalyze the title reaction on a gram-scale with excellent enantioselectivity.

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