Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
College of Pharmacy, Third Military Medical University, Shapingba, Chongqing 400038, China.
Org Lett. 2019 Sep 6;21(17):7184-7188. doi: 10.1021/acs.orglett.9b02944. Epub 2019 Aug 26.
A double catalytic system combining 2-mercaptobenzoic acid and a chiral phase transfer substance was disclosed for the intermolecular cross Rauhut-Currier reaction of 2-cyclopentenone and isatin-based alkylidene malononitriles. The resulting chiral adducts were sequentially assembled with diverse electron-deficient olefins to furnish highly enantioenriched cyclohexane derivatives (up to 96:4 er, >19:1 dr). A similar catalytic system of 2-mercaptobenzoic acid and quinine was further developed for the reaction of 2-cyclopentenone and α-cyano chalcones (up to 96.5:3.5 er).
一种双催化体系，结合 2-巯基苯甲酸和手性相转移物质，用于 2-环戊烯酮和基于靛红的亚烷基丙二腈的分子间交叉 Rauhut-Currier 反应。所得手性加合物与各种缺电子烯烃连续组装，得到高对映过量的环己烷衍生物（高达 96:4 的对映体过量，>19:1 的 dr）。进一步开发了 2-巯基苯甲酸和奎宁的类似催化体系，用于 2-环戊烯酮和α-氰基查尔酮的反应（高达 96.5:3.5 的对映体过量）。
