Highly regio-, diastereo- and enantioselective one-pot gold/chiral Brønsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines.
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.
Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong, PR China.
Xin-Yuan
XY
Liu
Ya-Ping
YP
Xiao
Fung-Ming
FM
Siu
Li-Chen
LC
Ni
Yong
Y
Chen
Lin
L
Wang
Chi-Ming
CM
Che
D000143:Acids / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006046:Gold / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000143:Acids; D000480:Alkynes; D000588:Amines; D001547:Benzaldehydes; D011804:Quinolines; D006046:Gold; C542964:1,2,3,4-tetrahydroquinoline