Issue 18, 2005
From the journal:

Organic & Biomolecular Chemistry

Enantioselective synthesis of (+)(R)- and (−)(S)-nicotine based on Ir-catalysed allylic amination†

Carolin Welter,a   Rosa M. Moreno,a   Stephane Streiffa  and  Günter Helmchen*a  

* Corresponding authors

a Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany
E-mail: g.helmchen@urz.uni-heidelberg.de
Fax: 49 6221 544205
Tel: 49 6221 8401

Abstract

The synthesis of nicotine with enantiomeric excess of >99% ee was accomplished by asymmetric Ir-catalysed allylic amination followed by ring closing metathesis and racemisation-free double bond reduction.

Graphical abstract: Enantioselective synthesis of (+)(R)- and (−)(S)-nicotine based on Ir-catalysed allylic amination

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Article information

DOI
https://doi.org/10.1039/B508634E
Article type
Communication
Submitted
20 Jun 2005
Accepted
01 Aug 2005
First published
11 Aug 2005

Org. Biomol. Chem., 2005,3, 3266-3268

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Enantioselective synthesis of (+)(R)- and (−)(S)-nicotine based on Ir-catalysed allylic amination

C. Welter, R. M. Moreno, S. Streiff and G. Helmchen, Org. Biomol. Chem., 2005, 3, 3266 DOI: 10.1039/B508634E

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