One-Pot Synthesis of Polyfunctionalized 4H-Chromenes and Dihydrocoumarins Based on Copper(II) Bromide-Catalyzed C-C Coupling of Benzylic Alcohols with Ketene Dithioacetals
One-Pot Synthesis of Polyfunctionalized 4H-Chromenes and Dihydrocoumarins Based on Copper(II) Bromide-Catalyzed C-C Coupling of Benzylic Alcohols with Ketene Dithioacetals
复制标题
溴化铜催化苯甲醇与烯酮二硫代缩醛的 C-C 偶联一锅法合成多官能化 4H-色烯和二氢香豆素
DOI：
10.1002/adsc.201000062
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发表时间：
2010-07-01
影响因子：
5.4
通讯作者：
Liu, Qun
中科院分区：
文献类型：
--
作者：
Liang, Deqiang;Wang, Mang;Liu, Qun
多官能化的4 H-色烯3和二氢香豆素4的合成已经从相同的底物开发。通过溴化铜（II）（0.3当量）催化，容易获得的烯酮二硫代缩醛1与2-（羟甲基）苯酚2在二氯甲烷溶剂中的反应导致4 H-色烯3的高产率至优异的产率，而3，4-反式-二取代的二氢香豆素4通过延长反应时间或将溶剂从二氯甲烷改变为乙腈以高产率和高非对映选择性获得。
The synthesis of polyfunctionalized 4H-chromenes 3 and dihydrocoumarins 4 has been developed from the same substrates. Catalyzed by copper(II) bromide (0.3 equiv.), the reactions of the easily available ketene dithioacetals 1 with 2-(hydroxymethyl)phenols 2 lead to 4H-chromenes 3 in high to excellent yields in dichloromethane solvent, whereas, 3,4-trans-disubstituted dihydrocoumarins 4 are obtained in high yields with high diastereoselectivities by prolonging the reaction time or changing the solvent from dichloromethane to acetonitrile.