ol8b01886_si_001.pdf (17.64 MB)
Palladium/N‑Heterocyclic Carbene (NHC)-Catalyzed Asymmetric [3 + 2] Cycloaddition Reaction of Vinyl Epoxides with Allenic Amides
journal contributionposted on 2018-08-06, 15:03 authored by Wan-Ying Wang, Jing-Yu Wu, Qing-Rong Liu, Xiu-Yan Liu, Chang-Hua Ding, Xue-Long Hou
Allenic amides are successfully developed as dipolarophiles to react with vinyl epoxides under Pd-catalysis. The chiral NHC showed its unique role as the ligand in this asymmetric [3 + 2] cycloaddition. Chiral tetrahydrofurans bearing three functional groups (monosubstituted alkene, tetrasubstituted enolether, and amide) and vicinal tertiary and quaternary stereocenters were obtained in high yields with high diastereo- and enantioselectivities.
vicinaltetrasubstituted enoletherAllenic Amides Allenic amidesliganddiastereoAsymmetricChiral tetrahydrofuransvinyl epoxidescycloadditionmonosubstituted alkeneroleCarbenePalladiumdipolarophileHeterocyclicquaternary stereocentersVinyl Epoxideschiral NHCyieldPd-catalysienantioselectivitieCycloaddition