Synfacts 2009(2): 0210-0210  
DOI: 10.1055/s-0028-1087595
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Aza-Cope Rearrangement

Contributor(s): Benjamin List, Olga Lifchits
M. Rueping*, A. P. Antonchick
Johann Wolfgang Goethe-Universität, Frankfurt am Main, Germany
Further Information

Publication History

Publication Date:
22 January 2009 (online)


A catalytic asymmetric 2-aza-Cope rearrangement was achieved by ­Brønsted acid catalysis. The transformation is initiated by an in situ formation of the iminium ion 4 catalyzed by the chiral phosphoric acid 1. The resulting chiral ion pair undergoes a [3,3]-sigmatropic rearrangement to afford chiral imines 2 in good yield and er values of up to 97:3. The authors demonstrated that 2 could be derivatized to the free and protected homoallylic amines 5 and 6, respectively, in good yield and without any loss of enantiomeric excess.