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Synfacts 2010(7): 0798-0798  
DOI: 10.1055/s-0029-1220076
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Tetrahydroquinolines by Inverse Electron-Demand Aza-Diels-Alder Reaction

Contributor(s): Mark Lautens, Chit Tsui
M. Xie, X. Chen, Y. Zhu, B. Gao, L. Lin, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

The inverse electron-demand aza-Diels-Alder (IEDDA) reaction of N-aryl imines with electron-rich alkenes is a powerful method for constructing tetrahydroquinolines. The authors ­report an asymmetric three-component IEDDA ­reaction with cyclopentadiene as dienophile. Using Sc(OTf)3/N,N′-dioxide (L) as the catalyst, the ring-fused tetrahydroquinoline products 4 can be obtained in excellent yield, diastereo- and enantio­selectivity.