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Enantioselective Synthesis of Tetrahydroquinolines from 2-Aminochalcones via a Consecutive One-Pot Reaction Catalyzed by Chiral Phosphoric Acid

Do Young Park, So Young Lee, Jiye Jeon, Cheol-Hong Cheon*

*Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea, Email: cheonkorea.ac.kr

D. Y. Park, S. Y. Lee, J. Jeon, C.-H. Cheon, J. Org. Chem., 2018, 83, 12486-12495.

DOI: 10.1021/acs.joc.8b01709 (free Supporting Information)


Abstract

A chiral phosphoric acid as the sole catalyst enables an enantioselective synthesis of tetrahydroquinolines from 2-aminochalcones via chiral phosphoric acid-catalyzed dehydrative cyclization, followed by chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities.

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Hantzsch ester



Key Words

tetrahydroquinolines, Hantzsch ester, organocatalysis


ID: J42-Y2018