文献类型：期刊文献

英文题名：Enantioselective Synthesis of Spiroketals and Spiroaminals via Gold and Iridium Sequential Catalysis

作者：Yang, Wu-Lin[1,2];Shang, Xin-Yu[1,2];Luo, Xiaoyan[1,2];Deng, Wei-Ping[1,2,3]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]Zhejiang Normal Univ, Dept Chem, Minist Educ Adv Catalysis Mat, Key Lab, Jinhua 321004, Zhejiang, Peoples R China

年份：2022

卷号：61

期号：26

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20221912070960);WOS:【SCI-EXPANDED(收录号:WOS:000789999100001)，CCR-EXPANDED(收录号:WOS:000789999100001)】；

基金：=This work is supported by the National Natural Science Foundation of China (nos. 22171081, 21901072, and 22171082) and Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism. The authors thank the Research Center of Analysis and Test of ECUST for the assistance with the HRMS and NMR analyses.

语种：英文

外文关键词：Allylation; Asymmetric Synthesis; Cascade Reactions; Sequential Catalysis; Spiroketals; Spiroaminals

摘要：The enantioselective cascade reaction between racemic 2-(1-hydroxyallyl)phenols and alkynols/alkynamides was realized by using a gold and iridium sequential catalytic system. In this procedure, the in situ generated exocyclic vinyl ethers or enamides undergo the asymmetric allylation/spiroketalization with pi-ally-Ir amphiphilic species, which provides an efficient and straightforward access to spiroketals and spiroaminals with excellent enantioselectivities. Moreover, racemic 2-(1-hydroxyallyl)anilines were also suitable in this reaction along with a kinetic resolution process, affording enantioenriched spiroaminals and 2-(1-hydroxyallyl)anilines in good yields. The synthetic utility of this method has been demonstrated by efficient enantioselective synthesis of the analogue of Paecilospirone.