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Issue 85, 2019
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Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines

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Abstract

In this paper, a palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with azomethine imines has successfully been developed under mild reaction conditions, affording biologically interesting tetrahydropyrazoloisoquinoline derivatives in high to excellent yields and with excellent stereoselectivity. The reaction follows a tandem [3+2] cycloaddition/allylation/elimination of AcOH pathway. Allenyl carbinol acetates also reacted well with in situ generated azomethine imine under cocatalysis of Ag(I)/Pd(0) catalysts in a similar reaction pathway.

Graphical abstract: Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines

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Publication details

The article was received on 27 Aug 2019, accepted on 02 Oct 2019 and first published on 02 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC06670E
Chem. Commun., 2019,55, 12841-12844

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    Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines

    B. Mao, J. Zhang, Y. Xu, Z. Yan, W. Wang, Y. Wu, C. Sun, B. Zheng and H. Guo, Chem. Commun., 2019, 55, 12841
    DOI: 10.1039/C9CC06670E

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