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Communication | Special issue | Vol 80, No. 2, 2010, pp.765-771
Published online, 7th September, 2009
DOI: 10.3987/COM-09-S(S)66
Enantioselective Synthesis of 2-Aryl-2,3-dihydro-4-quinolones by Chiral Brønsted Acid Catalyzed Intramolecular Aza-Michael Addition Reaction

Zhen Feng, Qing-Long Xu, Li-Xin Dai, and Shu-Li You*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 354 Finglin Road, Shanghai 200032, China

Abstract

Asymmetric intramolecular aza-Michael addition of activated α,β-unsaturated ketones catalyzed by chiral N-triflyl phosphoramide was realized. Enantioenriched 2-aryl-2,3-dihydroquinolin-4-ones can be obtained in excellent yields (77-98%) with up to 82% ee.