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

✍ Scribed by Martin Gärtner; Dr. Robert Weihofen; Prof. Dr. Günter Helmchen

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 512 KB
Volume: 17
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.201100649

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✦ Synopsis

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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