Chiral Bidentate Phosphoramidite-Pd Catalyzed Asymmetric Decarboxylative Dipolar Cycloaddition for Multistereogenic Tetrahydrofurans with Cyclic <i>N</i>-Sulfonyl Ketimine Moieties
Hao-Peng Lv, Xiaopeng Yang, Bailin Wang, Hao‐Di Yang, Xing‐Wang Wang, Zheng Wang
Abstract
An asymmetric [3 + 2] cycloaddition of vinyl ethylenecarbonates (VECs) and (E)-3-arylvinyl substituted benzo[d] isothiazole 1,1-dioxides has been developed using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst, providing a wide variety of chiral multistereogenic vinyltetrahydrofurans in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).
Topics & Concepts
ChemistryPhosphoramiditeCycloadditionSulfonylCatalysis1,3-Dipolar cycloadditionDenticityEnantioselective synthesisOrganic chemistryCombinatorial chemistryStereochemistryCrystal structureOligonucleotideBiochemistryDNAAlkylCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods