Zinc-Catalyzed Enantioselective [3 + 3] Annulation for Synthesis of Chiral Spiro[indoline-3,4′-thiopyrano[2,3-b]indole] Derivatives
Tiantian Liu, Yu Chen, Guang‐Jian Mei, Yuan‐Zhao Hua, Shi‐Kun Jia, Min‐Can Wang
Abstract
With a dinuclear zinc-ProPhenol complex as a catalyst, an efficient and novel [3 + 3] annulation of indoline-2-thiones and isatylidene malononitriles has been successfully developed via the Brønsted base and Lewis acid cooperative activation model. This practical methodology gives access to a broad range of chiral spiro[indoline-3,4′-thiopyrano[2,3-b]indole] derivatives in good yields with excellent levels of enantioselectivities (up to 88% yield and 99% ee).
Topics & Concepts
IndolineEnantioselective synthesisAnnulationIndole testCatalysisChemistryZincStereochemistryCombinatorial chemistryOrganic chemistryAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions