Enantioselective Synthesis of Bispiro[indanedione-oxindole-cyclopropane]s through Organocatalytic [2+1] Cycloaddition
Zhi-Feng Hao, Shijie Zhu, Yong‐Jia Hao, Wenhui Zhang, Ying Zhou, You‐Ping Tian, Chuan-Wen Lei
Abstract
A series of compounds featuring a novel bispiro[indanedione-oxindole-cyclopropane] moiety have been synthesized through a squaramide-catalyzed [2+1] cycloaddition reaction. The tandem Michael-alkylation reaction of 2-arylidene-1,3-indanediones with 3-bromooxindoles furnished the cycloadducts in high yields with excellent diastereo- and enantioselectivities. The ammonium ylide in the catalytic process, as a key intermediate, was revealed by the high-resolution mass spectrometry study.
Topics & Concepts
SquaramideCycloadditionCyclopropaneEnantioselective synthesisOxindoleYlideMoietyChemistryCatalysisAlkylationMichael reactionOrganic chemistryStereochemistryOrganocatalysisMedicinal chemistryRing (chemistry)Cyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions