Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2006(1): 0029-0029
DOI: 10.1055/s-2005-921694
DOI: 10.1055/s-2005-921694
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (+)(R)- and (-)(S)-Nicotine via Enantioselective Ir-Catalyzed Allylic Amination
C. Welter, R. M. Moreno, S. Streiff, G. Helmchen*
Universitat Heidelberg, Germany
Further Information
Publication History
Publication Date:
16 December 2005 (online)
![](https://www.thieme-connect.de/media/synfacts/200601/lookinside/thumbnails/10.1055-s-2005-921694-1.jpg)
Significance
The synthesis of (S)-nicotine via enantioselective allylic amination is achieved by Ir catalysts followed by ring-closing metathesis as the key steps. A closer examination of the ligand effect in Ir-catalyzed allylic amination shows that L2 yields the most promising enantiomeric excess (>99%). The synthesis of (R)-nicotine is also reported.