Enantioselective 1,3-Dipolar Cycloaddition of Methyleneindolinones with α-Diazomethylphosphonate to Access Chiral Spiro-phosphonylpyrazoline-oxindoles Catalyzed by Tertiary Amine Thiourea and 1,5-Diazabicyclo[4.3.0]non-5-ene

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A methodology to access chiral 3,3'-spiro-phosphonylpyrazoline oxindoles via an asymmetric 1,3-dipolar cycloaddition reaction of substituted methyleneindolinones with α-diazomethylphosphonate in the catalysis of tertiary amine thiourea and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) has been established. This method exhibits high functional group compatibility, where a wide range of methyleneindolinones with various substituents and heterocyclic rings are accommodated by this reaction. The resulting chiral 3,3'-spiro-phosphonylpyrazoline oxindoles can be further transformed into spiro-phosphonylcyclopropane oxindoles by ring contraction.