Chemodivergent Sulfonylation of Enynones via Ionic and Radical Addition Modes of Sulfinic Acids.
Divya BhattHun Young KimKyungsoo OhPublished in: Organic letters (2023)
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.