Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers
Xu Chen, Ilan Marek
Abstract
Abstract A highly regio‐ and diastereoselective nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl ketones and cyclopropyl carbinol derivatives using TMSBr, DMPSCl and TMSN 3 as nucleophiles has been developed. A variety of acyclic tertiary alkyl bromides, chlorides and azides were therefore prepared with excellent diastereopurity. The substitution occurs at the most substituted quaternary carbon center in a stereoinvertive manner, which may be attributed to the existence of a bicyclobutonium species.
Topics & Concepts
StereocenterChemistryNucleophileNucleophilic substitutionAlkylSubstitution reactionMedicinal chemistryCarbon fibersQuaternary carbonOrganic chemistryStereochemistryEnantioselective synthesisCatalysisComposite numberComposite materialMaterials scienceCyclopropane Reaction MechanismsClick Chemistry and ApplicationsChemical Synthesis and Analysis