Rh(<scp>ii</scp>)-catalyzed Doyle–Kirmse reaction: access to unprotected 3-allyl/3-allenyl-3-(thio)oxindoles
Xunbo Lu, Kaiyuan Yang, Xinyu Xu, Siyu Sun, Shanqing Feng, Muhammad Adnan Bashir, Fangpeng Liang, Jie Lin, Guoling Huang
Abstract
catalytic Doyle-Kirmse reaction to furnish the oxindole core, bearing unbiased NH as well as a quaternary stereogenic center at the 3-position, in good to excellent yields under mild conditions. These reactions are concise, practical, atom-economic, and highly efficient, and feature a TON of up to 3700. Moreover, a non-radical pathway was observed in this approach.
Topics & Concepts
StereocenterOxindoleChemistryCatalysisThio-Total synthesisCombinatorial chemistryBaylis–Hillman reactionCore (optical fiber)Medicinal chemistryStereochemistryOrganic chemistryEnantioselective synthesisComputer scienceTelecommunicationsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesCyclopropane Reaction Mechanisms