Catalytic Asymmetric Pictet–Spengler Reactions via Sulfenyliminium Ions

Authors

  • Martin J. Wanner,

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

    1. Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands, Fax: (+31) 20-525-5670
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  • Kimberly R. de Cuba,

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

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

    1. Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands, Fax: (+31) 20-525-5670
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  • This research was supported financially by the National Research School Combination Catalysis (NRSC-C). We thank R. Z. Boerleider and P. Hauwert for their help in the synthesis of the catalysts.

Abstract

original image

From cations to chiral products: β-Carbolines can be synthesized with good enantioselectivity by the title reaction catalyzed by a chiral binol-derived Brønsted acid (see scheme, BHT=3,5-di(tert-butyl)-4-hydroxytoluene). The procedure commences from tryptamine and can be scaled up readily, as both the installment and the removal of the auxiliary proceed in high yield under mild conditions.

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