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Synfacts 2007(6): 0587-0587
DOI: 10.1055/s-2007-968571
DOI: 10.1055/s-2007-968571
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Organo-Catalyzed Synthesis of 1,2-Dihydroquinolines
H. Li, J. Wang, H. Xie, L. Zu, W. Jiang, E. N. Duesler, W. Wang*
University of New Mexico, Albuquerque, USA
Further Information
Publication History
Publication Date:
22 May 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200706/lookinside/thumbnails/10.1055-s-2007-968571-1.jpg)
Significance
A diphenylprolinol TES-ether-catalyzed synthesis of 1,2-dihydroquinolines in high yields and good to excellent enantioselectivities is reported. The reaction follows a path involving formation of a chiral prolinol enamine intermediate of the α,β-unsaturated aldehyde followed by a Michael addition and an intramolecular aldol reaction with the ortho-aminobenzaldehyde. The scope of the reaction has been reasonably extensively investigated regarding the variation of the unsaturated aldehyde component but not with respect to the aminobenzaldehyde system.