Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes
Tereza Pavlíčková, Yannick Stöckl, Ilan Marek
Abstract
Implementing the use of alkynyllithium reagents in a stereospecific 1,2-metalate rearrangement-mediated ring opening of polysubstituted cyclopropyl boronic esters provides a variety of tertiary pinacol boranes bearing adjacent tertiary or quaternary carbon stereocenters with high levels of diastereomeric purity. The potential of this strategy was demonstrated through a selection of α- and γ-functionalization of the propargyl boronic esters.
Topics & Concepts
ChemistryStereocenterPinacolPropargylRing (chemistry)Surface modificationDiastereomerStereochemistryReagentEnantioselective synthesisOrganic chemistryMedicinal chemistryCombinatorial chemistryCatalysisPhysical chemistryOrganoboron and organosilicon chemistryCyclopropane Reaction MechanismsSynthetic Organic Chemistry Methods