Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters
Kaushalendra Patel, Veeranjaneyulu Lanke, Ilan Marek
Abstract
Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate.
Topics & Concepts
StereocenterChemistryStereospecificityNucleophileQuaternaryNucleophilic substitutionStereochemistrySubstitution (logic)Quaternary carbonInversion (geology)Enantioselective synthesisOrganic chemistryCatalysisPaleontologyStructural basinComputer scienceBiologyProgramming languageSynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms