Construction of Cyclopentanes Consisting of Five Stereocenters via NHC-Catalyzed Cascade Reactions of Enals with Oxindole-Dienones
Yadi Niu, Laiping Yao, Hongli Zhao, Xue Tang, Qian Zhao, Yuling Wu, Bo Han, Wei Huang, Gu Zhan
Abstract
Despite the widespread presence of the chiral cyclopentane motif, the asymmetric synthesis of cyclopentanes containing five stereocenters remains a formidable challenge. Here, we present an N -heterocyclic carbene (NHC)-catalyzed cascade reaction of enal and oxindole-dienone, which allows access to spiroxindole cyclopentanes featuring a complete set of chiral centers on the five-membered carbocycle. This strategy, characterized by the formation of multiple bonds and chiral centers, demonstrates a broad substrate scope, exclusive diastereoselectivity, and up to 99:1 er.
Topics & Concepts
CyclopentanesStereocenterOxindoleChemistryCyclopentaneOrganocatalysisCatalysisCarbeneCyclohexanesStereochemistryEnantioselective synthesisCombinatorial chemistryOrganic chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods