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Issue 90, 2019
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Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor–acceptor cyclopropanes with ketenes

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Abstract

When InBr3-EtAlCl2 (15–30 mol%) was used as a dual Lewis acid system to promote the formal [3+2]-cycloaddition of enantioenriched donor–acceptor cyclopropanes with ketenes, cyclopentanones were formed in good to excellent yields (84–99%, 18 examples), and with excellent transfer of chirality (15 examples, 90% ee to >99% ee).

Graphical abstract: Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor–acceptor cyclopropanes with ketenes

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Publication details

The article was received on 23 Sep 2019, accepted on 21 Oct 2019 and first published on 21 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC07477E
Chem. Commun., 2019,55, 13558-13561

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    Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor–acceptor cyclopropanes with ketenes

    M. Mondal, M. Panda, N. W. Davis, V. McKee and N. J. Kerrigan, Chem. Commun., 2019, 55, 13558
    DOI: 10.1039/C9CC07477E

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