Asymmetric Organocatalytic Henry Reaction

Authors

  • Tommaso Marcelli,

    1. Van't Hoff Institute of Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, Netherlands, Fax: (+31) 20-525-5670
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  • Richard N. S. van der Haas,

    1. Van't Hoff Institute of Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, Netherlands, Fax: (+31) 20-525-5670
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  • Jan H. van Maarseveen Dr.,

    1. Van't Hoff Institute of Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, Netherlands, Fax: (+31) 20-525-5670
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  • Henk Hiemstra Prof. Dr.

    1. Van't Hoff Institute of Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, Netherlands, Fax: (+31) 20-525-5670
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  • This research was financially supported by the National Research School Combination Catalysis (NRSC-C).

Abstract

original image

The nitroaldol (Henry) reaction between aromatic aldehydes and nitromethane can be carried out in high yields and enantiomeric excess by using a novel Cinchona-derived thiourea catalyst. Hydrogen-bond donors at the C6′ position in these organocatalysts are shown to induce preferential formation of one enantiomer.

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