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Issue 27, 2017
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One-pot asymmetric synthesis of a spiro[dihydrofurocoumarin/pyrazolone] scaffold by a Michael addition/I2-mediated cyclization sequence

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Abstract

An asymmetric formal one-pot reaction of 4-hydroxycoumarins with unsaturated pyrazolones has been developed by merging a chiral bifunctional organocatalyst with molecular iodine, which furnished a series of optically active spiro[dihydrofurocoumarin/pyrazolone] heterocycles with spiro quaternary stereogenic centers in moderate to excellent yields (up to 99%) with excellent diastereoselectivities (up to >99 : 1 dr) and good to excellent enantioselectivities (up to 99% ee). The application in the gram-scale synthesis of chiral spiro[dihydrofurocoumarin/pyrazolone] compounds was also successfully realized.

Graphical abstract: One-pot asymmetric synthesis of a spiro[dihydrofurocoumarin/pyrazolone] scaffold by a Michael addition/I2-mediated cyclization sequence

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Publication details

The article was received on 22 Apr 2017, accepted on 14 Jun 2017 and first published on 15 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB00986K
Citation: Org. Biomol. Chem., 2017,15, 5709-5718
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    One-pot asymmetric synthesis of a spiro[dihydrofurocoumarin/pyrazolone] scaffold by a Michael addition/I2-mediated cyclization sequence

    A. Xia, X. Zhang, C. Tang, K. Feng, X. Du and D. Xu, Org. Biomol. Chem., 2017, 15, 5709
    DOI: 10.1039/C7OB00986K

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