A Straightforward Synthesis
of (S)-Anabasine via the Catalytic, Enantio­selective
Vinylogous Mukaiyama-Mannich Reaction

David S. Giera; Marcel Sickert; Christoph Schneider

doi:10.1055/s-0029-1217026

PAPER

A Straightforward Synthesis of (S)-Anabasine via the Catalytic, Enantioselective Vinylogous Mukaiyama-Mannich Reaction

David S. Giera, Marcel Sickert, Christoph Schneider*
Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: schneider@chemie.uni-leipzig.de;

Abstract

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Abstract

The tobacco alkaloid (S)-anabasine was synthesized by a straightforward 4-step sequence with the catalytic enantioselective vinylogous Mannich reaction as a key step. Only 3 mol% of a structurally optimized chiral BINOL-based phosphoric acid was employed to control the absolute configuration of the natural product.

Key words

anabasine - piperidine - alkaloids - vinylogous Mannich reaction - Brønsted acid catalysis

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References

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A Straightforward Synthesis of (S)-Anabasine via the Catalytic, Enantio­selective Vinylogous Mukaiyama-Mannich Reaction

A Straightforward Synthesis of (S)-Anabasine via the Catalytic, Enantioselective Vinylogous Mukaiyama-Mannich Reaction