Enantioselective Synthesis of 3-Allylindolizines via Sequential Rh-Catalyzed Asymmetric Allylation and Tschitschibabin Reaction
Ke Li, Changkun Li
Abstract
The first highly regio- and enantioselective synthesis of 3-allylindolizines has been developed by the sequential Rh-catalyzed asymmetric allylation and Tschitschibabin reaction. Above the 20:1 branch/linear ratio, up to a 96% yield and 99% ee could be obtained with the help of tert-butyl-substituted chiral bisoxazolinephosphine ligand. In situ generated highly nucleophilic 2-alkylpyridinium ylides are utilized to undergo the asymmetric alkylation reaction before cyclization.
Topics & Concepts
Enantioselective synthesisChemistryYield (engineering)CatalysisNucleophileAlkylationLigand (biochemistry)Medicinal chemistryCombinatorial chemistryTsuji–Trost reactionStereochemistryOrganic chemistryReceptorMaterials scienceBiochemistryMetallurgySynthesis and Reactivity of HeterocyclesCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods