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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Cu(OTf)2-Catalyzed Three-Component Imino Diels-Alder Reaction Using Propenylbenzenes: Synthesis of 2,4-Diaryl Tetrahydroquinoline Derivatives

Author(s): Arnold R. Romero Bohorquez, Vladimir V. Kouznetsov and Michael P. Doyle

Volume 8 , Issue 1 , 2011

Page: [5 - 11] Pages: 7

DOI: 10.2174/157017811794557831

Price: $65


Copper(II) triflate mediated three-component [4+2]-cycloaddition reactions between anilines, benzaldehydes and trans-anethole or trans-isoeugenol are reported. A simple and efficient one-pot method for the synthesis of diverse 2,4-diaryl-1,2,3,4-tetrahydroquinolines under mild conditions in the presence of catalytic amounts (10 mol %) of Cu(OTf)2 was developed. Attempts toward an asymmetric imino Diels-Alder reaction are discussed.

Keywords: Copper(II) triflate catalyzed imino diels-alder reaction, multi-component reaction, 2,4-diaryl-1,2,3,4-tetrahydroquinolines, trans-anethole, trans-isoeugenol as electron-rich alkenes

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