4.7 Article

Phosphine-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Isoxazole-Based Alkenes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 3, Pages 2090-2099

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01948

Keywords

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Funding

  1. Natural Science Foundation of China [21572264, 21871293, 22071264]
  2. Chinese Universities Scientific Fund [2018TC052, 2018TC055, 2019TC085]

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A phosphine-catalyzed [3 + 2] annulation reaction has been developed in this study to synthesize multifunctional isoxazoles with moderate to good yields and diastereoselectivities. The use of a spirocyclic chiral phosphine catalyst resulted in up to 89% ee.
A phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.

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