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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Unlocking Oxidative Cross-Coupling between Four Nucleophiles: Synthesis of Spiropyrrolo[2,1-a]isoquinolines
Yong-Xing Tang1, Jun Ma1, Li-Sheng Wang1
1State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.
Abstract:
The oxidative cross-coupling of four nucleophiles, while intriguing for concurrently forming multiple C(X)-C bonds by the removal of several C(X)-H bonds, remains challenging and underexplored. Herein, we report that the convergent integration of two streams of two-component oxidation cross-couplings achieves the assembly of four nucleophiles in a highly self-sorting manner. By removal of 10 hydrogen atoms, an I2-DMSO-promoted reaction using 1,2,3,4-tetrahydroisoquinoline (THIQ), active methylene, and two molecules of arylmethyl ketones affords structurally novel 3D frameworks featuring a spiropyrrolo[2,1-a]isoquinoline core.
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