Highly regio-, diastereo- and enantioselective one-pot gold/chiral Bronsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines
Highly regio-, diastereo- and enantioselective one-pot gold/chiral Bronsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines
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DOI：
10.1039/c2ob25753j
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发表时间：
2012-01-01
影响因子：
3.2
通讯作者：
Che, Chi-Ming
中科院分区：
文献类型：
--
作者：
Liu, Xin-Yuan;Xiao, Ya-Ping;Che, Chi-Ming
报道了金（I）/布朗斯台德酸协同体系催化氨基苯甲醛或氨基苯酮与炔烃的一锅连续不对称反应。该过程提供了一种高效的合成光学活性四氢喹啉的方法，该四氢喹啉具有位于不同位置的一个或两个手性中心以及高度不同的官能团，收率良好至优异，并且具有高区域选择性、非对映选择性和对映选择性。关于立体化学对生物活性影响的初步研究表明这些光学活性四氢喹啉在药物发现过程中的潜在应用。
One-pot sequential asymmetric reactions of aminobenzaldehydes or aminophenones with alkynes catalysed by a gold(I)/Bronsted 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.