Issue 35, 2012
From the journal:

Organic & Biomolecular Chemistry

Highly regio-, diastereo- and enantioselective one-pot gold/chiral Brønsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines†

Xin-Yuan Liu,a   Ya-Ping Xiao,a   Fung-Ming Siu,a   Li-Chen Ni,a   Yong Chen,a   Lin Wanga  and  Chi-Ming Che*a  

* Corresponding authors

a Department of Chemistry, State Key Laboratory of Synthetic Chemistry, and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, P.R. China
E-mail: cmche@hku.hk
Fax: (+852)2857-1586

Abstract

One-pot sequential asymmetric reactions of aminobenzaldehydes or aminophenones with alkynes catalysed by a gold(I)/Brønsted acid cooperative system are reported. This process provides a highly efficient method for the synthesis of optically active tetrahydroquinolines, with one or two chiral centres at different positions as well as highly divergent functional groups, in good to excellent yields and with high regio-, diastereo- and enantioselectivities. A preliminary study on the effect of stereochemistry on biological activity suggests a potential application of these optically active tetrahydroquinolines in drug discovery processes.

Graphical abstract: Highly regio-, diastereo- and enantioselective one-pot gold/chiral Brønsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines

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Article information

DOI
https://doi.org/10.1039/C2OB25753J
Article type
Paper
Submitted
19 Apr 2012
Accepted
11 Jun 2012
First published
11 Jul 2012

Org. Biomol. Chem., 2012,10, 7208-7219

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Highly regio-, diastereo- and enantioselective one-pot gold/chiral Brønsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines

X. Liu, Y. Xiao, F. Siu, L. Ni, Y. Chen, L. Wang and C. Che, Org. Biomol. Chem., 2012, 10, 7208 DOI: 10.1039/C2OB25753J

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