Catalytic Enantioselective Synthesis of 2,3-Dihydrobenzo[<i>b</i>]oxepines via Asymmetric Oxetane Opening by Internal Carbon Nucleophiles
Tianyu Zhang, Han Zhuang, Luning Tang, Zhengyu Han, Wengang Guo, Hai Huang, Jianwei Sun
Abstract
An intramolecular C–C formation process based on catalytic asymmetric oxetane opening by carbon nucleophiles has been developed, which provides rapid access to a range of valuable enantioenriched 2,3-dihydrobenzo[b]oxepines. With the combination of Sc(OTf)3 and a Box ligand, good chemical efficiency and enantioselectivity were achieved under mild conditions. The products are also useful precursors to other valuable structures, such as the bicyclo[3.2.2]nonane derivatives.
Topics & Concepts
OxetaneNucleophileChemistryEnantioselective synthesisIntramolecular forceCatalysisLigand (biochemistry)Bicyclic moleculeStereochemistryRing (chemistry)NonaneCombinatorial chemistryCarbon fibersMedicinal chemistryOrganic chemistryMaterials scienceReceptorBiochemistryComposite materialComposite numberSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis