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.
J Org Chem. 2020 Aug 21;85(16):10760-10771. doi: 10.1021/acs.joc.0c01293. Epub 2020 Aug 12.
An asymmetric intramolecular Rauhut-Currier reaction of linear bis(enones) has been achieved via double activation catalysis of thiols and phase transfer substances, furnishing both enantioenriched cyclohexene and cyclopentene derivatives (up to 95% ee). Furthermore, the desymmetric version of prochiral substrates was developed under similar catalysis, producing the frameworks bearing an additional tertiary or even quaternary stereogenic center with moderate to excellent diastereo- and enantioselectivity (up to 95% ee, >19:1 dr).
通过硫醇和相转移物质的双重活化催化，实现了线性双烯酮的不对称分子内 Rauhut-Currier 反应，得到了手性环己烯和环戊烯衍生物（高达 95%的对映体过量）。此外，在手性底物的非对称版本的开发下，在相似的催化条件下，得到了具有额外的三级甚至四级立体中心的骨架，具有中等至优秀的非对映选择性和对映选择性（高达 95%的对映体过量，>19:1 的 dr）。
