Enantioselective Hydroarylation or Hydroalkenylation of Benzo[<i>b</i>]thiophene 1,1-Dioxides with Organoboranes
Fangdong Hu, Jie Jia, Ximing Li, Ying Xia
Abstract
An efficient protocol for the asymmetric hydroarylation and hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes has been developed. The combination of a rhodium(I) precatalyst and a chiral diene ligand constitutes the catalytic system, which enables the facile synthesis of 2,3-dihydrobenzo[b]thiophene 1,1-dioxides in good yields with high enantioselectivities. The merging of this asymmetric hydroarylation with the downstream alkylations delivers 2,3-dihydrobenzo[b]thiophene 1,1-dioxides that contain two continuous quaternary stereocenters with high enantioselectivities in a diastereodivergent manner.
Topics & Concepts
StereocenterChemistryThiopheneEnantioselective synthesisCatalysisLigand (biochemistry)Combinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryReceptorBiochemistryAsymmetric Hydrogenation and CatalysisChemical Synthesis and ReactionsSulfur-Based Synthesis Techniques