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Synfacts 2005(3): 0323-0323
DOI: 10.1055/s-2005-921644
DOI: 10.1055/s-2005-921644
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
MCR of Organoaluminium, Isoprene, Aldehydes and Amines
K. Kojima, M. Kimura, Y. Tamaru*
Nagasaki University, Japan
Further Information
Publication History
Publication Date:
22 November 2005 (online)
![](https://www.thieme-connect.de/media/synfacts/200503/lookinside/thumbnails/10.1055-s-2005-921644-1.jpg)
Significance
This is a nice extension on the previous three-component connection of organozincs, dienes and aldehydes (Y. Tamaru et al. Angew. Chem. Int. Ed. 1999, 38, 3386-3388). In this example the use of the often less electrophilic imine provides E-homoallylamines with very high selectivity (up to 20:1, E:Z). Electron-donating and -withdrawing substituents were tolerated in the aromatic aldehyde portion. The presence of Me3Al was necessary for the methyl addition and Ph2Zn was used for the phenyl addition.