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Enantioselective synthesis of dihydroquinazolinone derivatives catalyzed by a chiral organocatalyst

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Abstract

The asymmetric condensation/amine addition cascade sequence of 2-aminobenzamide and aldehydes, catalyzed by a novel chiral organocatalyst, was realized. The organocatalyst was found to be very effective and highly enantioselective for such cascade reactions at room temperature, affording 2,3-dihydroquinazolinones in excellent yields (up to 99%) with enantiomeric excesses of up to 97%. The best level of stereocontrol was obtained for aromatic/aliphatic aldehydes with ortho, para or meta substituents.

Graphical abstract: Enantioselective synthesis of dihydroquinazolinone derivatives catalyzed by a chiral organocatalyst

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Publication details

The article was received on 14 Feb 2017, accepted on 28 Jun 2017 and first published on 28 Jun 2017


Article type: Paper
DOI: 10.1039/C7NJ00538E
Citation: New J. Chem., 2017, Advance Article
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    Enantioselective synthesis of dihydroquinazolinone derivatives catalyzed by a chiral organocatalyst

    S. Ayyanar, P. K. Vijaya, M. Mariyappan, V. Ashokkumar, V. Sadhasivam, S. Balakrishnan, C. Chinnadurai and S. Murugesan, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ00538E

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