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Issue 8, 2016
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Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis

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Abstract

An enantioselective one-pot Michael addition/hydroalkoxylation reaction between 2-hydroxy-1,4-naphthoquinones and alkyne-tethered nitroalkenes catalyzed by a cinchona-derived squaramide and a silver(I) salt has been developed. The sequential protocol provides a direct access to 4H-pyranonaphthoquinones in moderate to very good yields and good to excellent enantioselectivities at a very low catalyst loading (0.5 mol%) of the squaramide.

Graphical abstract: Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis

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Publication details

The article was received on 19 Nov 2015, accepted on 02 Dec 2015 and first published on 03 Dec 2015


Article type: Communication
DOI: 10.1039/C5CC09592A
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Citation: Chem. Commun., 2016,52, 1669-1672

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    Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis

    U. Kaya, P. Chauhan, D. Hack, K. Deckers, R. Puttreddy, K. Rissanen and D. Enders, Chem. Commun., 2016, 52, 1669
    DOI: 10.1039/C5CC09592A

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