Organo/Silver Dual Catalytic (3 + 2)/Conia-Ene Type Cyclization: Asymmetric Synthesis of Indane-Fused Spirocyclopenteneoxindoles
Dong‐Ai Li, Xiang‐Hong He, Xue Tang, Yuling Wu, Hongli Zhao, Gu He, Cheng Peng, Bo Han, Gu Zhan
Abstract
Developing efficient strategies to synthesize spirocyclopenteneoxindoles is an attractive target due to their potential biological activity. This work described the thiourea/silver dual catalytic (3 + 2)/Conia-ene type reaction of 2-(2-oxoindolin-3-yl)malononitrile with ortho-ethynyl substituted nitrostyrene. The reaction features mild conditions and good atom- and step-economy. Three new C–C bonds were formed within one synthetic step, providing the indane-fused spirocyclopenteneoxindoles in good yields, with excellent chemo-, regio-, and stereoselectivity.
Topics & Concepts
IndaneChemistryMalononitrileThioureaCatalysisStereoselectivityCombinatorial chemistryEne reactionAtom economyMedicinal chemistryStereochemistryOrganic chemistryAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsTraditional and Medicinal Uses of Annonaceae