Chemodivergent Sulfonylation of Enynones via Ionic and Radical Addition Modes of Sulfinic Acids
Divya Bhatt, Hun Young Kim, Kyungsoo Oh
Abstract
Different addition modes of sulfinic acids were developed for the chemodivergent sulfonylation of enynones, where the ionic sulfonylation to an alkyne moiety of enynones was effected through a salt-controlled syn -addition pathway. The radical sulfonylation of an alkene moiety also provided the stereodefined sulfonylated alkenes. A one-pot tandem sequence of the Ti(O i -Pr) 4 -catalyzed α-vinyl aldol condensation of ( E )-β-chlorovinyl ketones followed by the chemodivergent sulfonylations was also explored, allowing for ready access to highly substituted dienes and enynes.
Topics & Concepts
ChemistryMoietyAlkeneSulfinic acidAlkyneAldol reactionTandemAldol condensationSalt (chemistry)Sequence (biology)Ionic bondingOrganic chemistryMedicinal chemistryCatalysisIonComposite materialMaterials scienceBiochemistrySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions