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Z. Naturforsch. 2012,
67b, 1021 – 1029
doi:10.5560/ZNB.2012-0183
Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones
1 RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, D-52074 Aachen, Germany
2 Goethe University Frankfurt, Institut of Inorganic and Analytical Chemistry, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, Germany
Reprint requests to Prof. Dr. Magnus Rueping. Fax: +49 241 8092665. E-mail:
magnus.rueping@rwth-aachen.de
Received July 5, 2012 / published online October 8, 2012
Dedicated to Professor Heribert Offermanns on the occasion of his 75th birthday
The enantioselective synthesis of 2-aryl-substituted 2,3-dihydroquinolin-4-ones, a class of heterocyclic compounds with interesting biological activities, has been achieved through a Brønsted acid-catalyzed enantioselective intramolecular Michael addition. The products are available in moderate to high yields and with good enantioselectivities.
Key words: aza-Michael Addition, Brønsted Acid, N-Triflyl Phosphoramide, Dihydroquinolin-4-ones