Asymmetric Synthesis of 3,3′-Tetrahydrofuryl Spirooxindoles via Palladium-Catalyzed [3+2] Cycloadditions of Methyleneindolinones with Vinylethylene Carbonates
Junwei Wang, Lei Zhao, Quanjin Rong, Cheng Lv, Lu Yu, Xiang Pan, Lin Zhao, Lihong Hu
Abstract
A palladium-catalyzed asymmetric [3+2] cycloaddition reaction of methyleneindolinones with vinylethylene carbonates has been successfully developed, which provides a highly efficient method for the synthesis of structurally diverse 3,3'-tetrahydrofuryl spirooxindoles in high yields (≤99%) with excellent stereoselectivities (>20:1 dr, ≤99% ee). Furthermore, this methodology shows a wide substrate scope and high utility in diversity-oriented synthesis.
Topics & Concepts
ChemistryCatalysisPalladiumCycloadditionCombinatorial chemistrySubstrate (aquarium)Scope (computer science)Reaction conditionsOrganic chemistryComputer scienceGeologyProgramming languageOceanographyAsymmetric Synthesis and CatalysisOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions