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Chemistry. 2011 Dec 2;17(49):13800-5. doi: 10.1002/chem.201102333. Epub 2011 Nov 14.

Asymmetric synthesis of tetrahydroquinolines with quaternary stereocenters through the Povarov reaction.

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  • 1Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.


The asymmetric Povarov reaction with α-alkyl styrenes as dienophiles was catalyzed by an N,N'-dioxide L4-Sc(OTf)(3) complex. Enantiopure tetrahydroquinoline derivatives with a quaternary stereocenter at the C4 position were synthesized for the first time. A wide variety of α-alkyl styrenes and N-aryl aldimines were tolerated in the reaction, to give excellent diastereo- (up to 99:1 d.r.) and enantioselectivities (92 to >99% ee). In addition, the reaction could be performed on the gram scale without any loss of yield, diastereoselectivity, or enantioselectivity. An intermolecular hydrogen-shift reaction was found to be a side reaction, which offered a method to synthesize the corresponding quinoline derivatives with chiral quaternary sterocenters.

Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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