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Issue 36, 2017
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Phosphine-catalyzed [3 + 2] annulation reaction: highly regio- and diastereoselective synthesis of 2-azaspiro[4.4]nonene-1,3-diones

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Abstract

A novel phosphine-catalyzed [3 + 2] annulation of γ-substituted allenoates with succinimides was developed, which was successfully applied to the synthesis of 2-azaspiro[4.4]nonene-1,3-dione derivatives. The reaction afforded the desired products in moderate to high yields (up to 96%) with excellent regioselectivities and diastereoselectivities (up to >99 : 1 dr). A plausible reaction mechanism has also been proposed based on previous literature.

Graphical abstract: Phosphine-catalyzed [3 + 2] annulation reaction: highly regio- and diastereoselective synthesis of 2-azaspiro[4.4]nonene-1,3-diones

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Publication details

The article was received on 07 Aug 2017, accepted on 24 Aug 2017 and first published on 24 Aug 2017


Article type: Communication
DOI: 10.1039/C7OB01957B
Citation: Org. Biomol. Chem., 2017,15, 7523-7526
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    Phosphine-catalyzed [3 + 2] annulation reaction: highly regio- and diastereoselective synthesis of 2-azaspiro[4.4]nonene-1,3-diones

    W. Luo, H. Hu, S. Nian, L. Qi, F. Ling and W. Zhong, Org. Biomol. Chem., 2017, 15, 7523
    DOI: 10.1039/C7OB01957B

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