Palladium‐Catalyzed Asymmetric [3+2] Cycloaddition of Vinylethylene Carbonates with 2‐Arylidene‐1,3‐Indandiones: Synthesis of Tetrahydrofuran‐Fused Spirocyclic 1,3‐Indandiones
Huihui Zhang, Xing Gao, Feng Jiang, Wangyu Shi, Wei Wang, Yongjun Wu, Cheng Zhang, Xueyan Shi, Hongchao Guo
Abstract
An asymmetric [3+2] cycloaddition of 2‐arylidene‐1,3‐indandiones with vinylethylene carbonates (VECs) had been achieved in the presence of Pd 2 dba 3 · CHCl 3 and axially chiral phosphoramidite ligand. The reaction of various substituted VECs and 2‐arylidene‐1,3‐indandiones proceeded smoothly under mild conditions, giving the highly functionalized spirocyclic 1,3‐indanedione derivatives in good to excellent yield with moderate diastereoselectivity and high enantioselectivity. The reaction on the gram scale had also been demonstrated.
Topics & Concepts
ChemistryCycloadditionTetrahydrofuranYield (engineering)PhosphoramiditePalladiumCatalysisLigand (biochemistry)Medicinal chemistryOrganic chemistryReceptorSolventOligonucleotideBiochemistryMetallurgyDNAMaterials scienceAsymmetric Synthesis and CatalysisCyclopropane Reaction MechanismsOxidative Organic Chemistry Reactions