Organocatalytic Stereoselective Synthesis of Fluorinated 3,3′-Linked Bisoxindoles

• DOI: 10.1021/acs.joc.7b03084
• Publication Date: 2018-01-09T21:07:59Z
• Authors: Max Moskowitz; Kaluvu Balaraman; Christian Wolf
• Keywords: Indoles; Halogenation; Hydrocarbons, Fluorinated; Molecular Structure; Temperature; Stereoisomerism; 01 natural sciences; Catalysis; Oxindoles; 0104 chemical sciences

A highly diastereoselective organocatalytic method that produces 3-fluoro-3'-hydroxy-3,3'-bisoxindoles and the corresponding 3-fluoro-3'-amino derivatives having two adjacent chirality centers from fluorooxindoles and isatins in high yields is described. The reaction occurs in protic solvents at room temperature, it can be upscaled without compromising yield and stereoselectivity, and chromatographic product purification is not required.