Atroposelective Kinetic Resolution of 8<i>H</i>-Indeno[1,2-<i>c</i>]thiophen-8-ols via Pd-Catalyzed C–C Bond Cleavage Reaction
Junwei Xi, Han Yang, Lin Li, Xue Zhang, Chunyu Li, Zhenhua Gu
Abstract
The present work demonstrates a palladium-catalyzed kinetic resolution/ring-opening reaction of 8H-indeno[1,2-c]thiophen-8-ols. The reaction proceeds in a highly regioselective manner, and both optically active thiophene-phenyl atropisomers and stereogenic 8H-indeno[1,2-c]thiophen-8-ols were obtained with high enantiomeric excesses. The synthetic applications of the obtained thiophenyl atropisomers were briefly investigated.
Topics & Concepts
ChemistryStereocenterAtropisomerKinetic resolutionRegioselectivityCatalysisThiopheneEnantiomerRing (chemistry)PalladiumBond cleavageMedicinal chemistryCleavage (geology)Kinetic energyStereochemistryOrganic chemistryEnantioselective synthesisGeotechnical engineeringQuantum mechanicsEngineeringFracture (geology)PhysicsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chirality