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Issue 77, 2015
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Phosphine-catalyzed [4 + 2] cycloaddition of unsaturated pyrazolones with allenoates: a concise approach toward spiropyrazolones

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Abstract

A MePPh2-catalyzed [4 + 2] cycloaddition reaction of unsaturated pyrazolones with allenoates was described. The reaction affords the spiropyrazolone derivatives in moderate to excellent yields with moderate to good diastereoselectivities under mild conditions. Using thiourea-based bifunctional phosphines as chiral catalysts, an asymmetric variant of this [4 + 2] cycloaddition reaction has been achieved, giving chiral spiropyrazolone derivatives in moderate to excellent yields with moderate to excellent diastereoselectivities and excellent enantioselectivities (89–95% ee).

Graphical abstract: Phosphine-catalyzed [4 + 2] cycloaddition of unsaturated pyrazolones with allenoates: a concise approach toward spiropyrazolones

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Publication details

The article was received on 17 Jun 2015, accepted on 14 Jul 2015 and first published on 20 Jul 2015


Article type: Paper
DOI: 10.1039/C5RA11595G
Citation: RSC Adv., 2015,5, 62343-62347
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    Phosphine-catalyzed [4 + 2] cycloaddition of unsaturated pyrazolones with allenoates: a concise approach toward spiropyrazolones

    W. Yang, Y. Zhang, S. Qiu, C. Zhao, L. Zhang, H. Liu, L. Zhou, Y. Xiao and H. Guo, RSC Adv., 2015, 5, 62343
    DOI: 10.1039/C5RA11595G

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