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Synfacts 2006(10): 1061-1061
DOI: 10.1055/s-2006-949377
DOI: 10.1055/s-2006-949377
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement
M. Sugiura, C. Mori, S. Kobayashi*
The University of Tokyo, Japan
Further Information
Publication History
Publication Date:
21 September 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200610/lookinside/thumbnails/10.1055-s-2006-949377-1.jpg)
Significance
The enantioselective transfer aminoallylation catalyzed by a Brønsted acid leading to homoallylic primary amines 6 is described. Starting from aldehyde 1 and chiral homoallylamine 2, an imine-intermediate 3 is formed, which can undergo a 2-aza-Cope rearrangement to imine 4. Finally, the homoallylic amine 6 is released after cleavage of the imine bond with hydroxylamine. The authors have employed camphorsulfonic acid as a catalyst, leading to homoallylic amines 6 in good yields and excellent enantiomeric ratios.