Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems
André U. Augustin, Sergio Di Silvio, Ilan Marek
Abstract
Herein, we present the formation of acyclic frameworks bearing two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This holistic approach involves a regio- and diastereoselective hydro- or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes of the latter via the addition of nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivered the title compounds.
Topics & Concepts
StereocenterChemistryVicinalNucleophileCleavage (geology)StereochemistryBond cleavageCarbon fibersOrganic chemistryEnantioselective synthesisCatalysisPaleontologyBiologyFracture (geology)Composite numberComposite materialMaterials scienceCyclopropane Reaction MechanismsOrganoboron and organosilicon chemistrySynthetic Organic Chemistry Methods