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Enantioselective Syntheses of 2,5-Disubstituted Pyrrolidines Based on Iridium-Catalyzed Allylic Aminations—Total Syntheses of Alkaloids from Amphibian Skins

Authors

  • Martin Gärtner,

    1. Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
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  • Dr. Robert Weihofen,

    1. Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
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  • Prof. Dr. Günter Helmchen

    Corresponding author
    1. Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
    • Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-544205
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Abstract

A broadly applicable route to trans-2,5-disubstituted pyrrolidines has been developed. Key steps are an asymmetric iridium-catalyzed allylic amination, a Suzuki–Miyaura coupling, and an intramolecular aza-Michael addition. Enantiomeric excesses in the range of 93–99 % ee have been achieved. Total syntheses of the alkaloids (−)-225 C, (+)- and (−)-223 H (xenovenine), (+)-223 AB, (+)-195 B, and (+)-223 R have been carried out as applications.

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