Rh(<scp>i</scp>)-catalyzed stereoselective desymmetrization of prochiral cyclohexadienones <i>via</i> highly <i>exo</i>-selective Huisgen-type [3 + 2] cycloaddition
Krishna Kumar Gollapelli, Vaibhav B. Patil, Allam Vinaykumar, Rambabu Chegondi
Abstract
-dig cyclization of carbonyl oxygen onto an activated alkyne resulting in a highly reactive metal-benzopyrylium intermediate, which readily undergoes intramolecular [3 + 2] annulation/hydration. Asymmetric induction is also achieved for the first time in Rh(i)-catalyzed 1,3-dipolar cycloaddition using an easily accessible chiral diene as the ligand.
Topics & Concepts
CycloadditionDesymmetrizationChemistryStereocenterIntramolecular forceStereoselectivityAnnulationStereochemistryAlkyneCatalysisCombinatorial chemistryEnantioselective synthesisOrganic chemistryCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods