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Issue 35, 2012
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Highly regio-, diastereo- and enantioselective one-pot gold/chiral Brønsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines

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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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Supplementary files

Article information


Submitted
19 Apr 2012
Accepted
11 Jun 2012
First published
11 Jul 2012

Org. Biomol. Chem., 2012,10, 7208-7219
Article type
Paper

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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