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Issue 8, 2018
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Organocatalytic asymmetric synthesis of compounds bearing both isoxazole and pyrazole moieties via 1,6-addition of pyrazol-5-ones to 3-methyl-4-nitro-5-alkenylisoxazoles

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Abstract

An efficient one-pot asymmetric synthesis of chiral compounds containing both isoxazole and pyrazole moieties has been developed. The bifunctional thiourea catalyzed asymmetric 1,6-addition of pyrazol-5-ones to 3-methyl-4-nitro-5-alkenylisoxazoles provided the corresponding acetylated chiral heterocycles after in situ treatment with AcCl/Et3N. The corresponding products were generated in good yields (72–90%) with high enantioselectivities (83–94% ee).

Graphical abstract: Organocatalytic asymmetric synthesis of compounds bearing both isoxazole and pyrazole moieties via 1,6-addition of pyrazol-5-ones to 3-methyl-4-nitro-5-alkenylisoxazoles

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Publication details

The article was received on 25 Jan 2018, accepted on 22 Feb 2018 and first published on 23 Feb 2018


Article type: Research Article
DOI: 10.1039/C8QO00084K
Citation: Org. Chem. Front., 2018,5, 1342-1347
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    Organocatalytic asymmetric synthesis of compounds bearing both isoxazole and pyrazole moieties via 1,6-addition of pyrazol-5-ones to 3-methyl-4-nitro-5-alkenylisoxazoles

    F. Li, W. Pei, J. Wang, J. Liu, J. Wang, M. Zhang, Z. Chen and L. Liu, Org. Chem. Front., 2018, 5, 1342
    DOI: 10.1039/C8QO00084K

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