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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

Über Kationen zu chiralen Produkten: β-Carboline entstehen mit guter Enantioselektivität in der durch eine chirale, von Binol abgeleitete Brønsted-Säure katalysierten Titelreaktion (siehe Schema, BHT=3,5-Di(tert-Butyl)-4-hydroxytoluol). Das Verfahren geht von Tryptamin aus, und größere Ansätze sind einfach möglich, da Einführen und Entfernen des Auxiliars unter milden Bedingungen in hoher Ausbeute gelingen.

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