Formal [4+1] Cyclization of <i>ortho</i>‐ or <i>para</i>‐Quinone Methides with 3‐Chlorooxindoles: Synthesis of 3,2′‐Tetrahydrofuryl Spirooxindoles
Xiaochen Tian, Xiaoli Zhang, Xiaohan Hou, Weiwu Ren, Xiaoyang Li, Fei Zhao, Houchao Tao, Yang Wang
Abstract
Abstract A base promoted formal [4+1] cycloaddition of ortho ‐ and para ‐quinone methides with 3‐chlorooxindoles is reported to afford various functionalized 3,2′‐tetrahydrofuryl spirooxindoles in high yields under mild conditions. An unexpected reversal in diastereoselectivity was observed from these two types of reactions. Computational studies have provided insight into the origin of diastereoselection, and different configurations of 1,4‐addition and 1,6‐addition at the oxindole carbanionic center are found to give rise to different diastereomers. The anti‐tumor activity of these structurally unique spirooxindole derivatives is reported.
Topics & Concepts
OxindoleChemistryDiastereomerCycloadditionQuinoneCombinatorial chemistryBase (topology)StereochemistryOrganic chemistryCatalysisMathematicsMathematical analysisSynthesis of Indole DerivativesBioactive Compounds and Antitumor Agents