Chiral Gold Phosphate Catalyzed Tandem Hydroamination/Asymmetric Transfer Hydrogenation Enables Access to Chiral Tetrahydroquinolines

Yu-Liu Du, Yue Hu, Yi-Fan Zhu, Xi-Feng Tu, Zhi-Yong Han* and Liu-Zhu Gong

*Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China, Email: hanzy2014ustc.edu.cn

Y.-L. Du, Y. Hu, Y.-F. Zhu, X.-F. Tu, Z.-Y. Han, L.-Z. Gong, J. Org. Chem., 2015, 80, 4754-4759.

DOI: 10.1021/acs.joc.5b00153

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Abstract

A highly efficient gold-catalyzed tandem hydroamination/asymmetric transfer hydrogenation provides tetrahydroquinolines in excellent yields and enantioselectivities in the presence of a chiral phosphate. In this reaction, the gold catalyst acts as a π-Lewis acid in the hydroamination step and as an effective chiral Lewis acid in the asymmetric hydrogen-transfer.

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Consecutive Intramolecular Hydroamination/Asymmetric Transfer Hydrogenation under Relay Catalysis of an Achiral Gold Complex/Chiral Brønsted Acid Binary System

Z.-Y. Han, H. Xiao, X.-H. Chen, L.-Z. Gong, J. Am. Chem. Soc., 2009, 131, 9182-9183.

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Key Words

tetrahydroquinolines, Hantzsch ester

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ID: J42-Y2015