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Synfacts 2006(1): 0029-0029  
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

Contributor(s): Victor Snieckus, Sunny Lai
C. Welter, R. M. Moreno, S. Streiff, G. Helmchen*
Universitat Heidelberg, Germany
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Publication History

Publication Date:
16 December 2005 (online)

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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.