A new one-pot synthesis of sulfoxides is presented. It involves the bora-ene reaction of sulfur dioxide and prop-2-ene-1-boronic esters, giving mixed anhydrides of sulfinic and boric acids. The latter react chemoselectively at the sulfur center with Grignard reagents in displacement reactions giving the corresponding prop-2-en-1-ylsulfoxides. Preliminary studies on the chirality transfer of enantiomerically enriched boronates to the sulfoxides are also presented.
Andrea Baccarini, Imad El Haddad, Mihnea Surdu, Lubna Dada, André Welti, Houssni Lamkaddam
Alkynes are found in a multitude of natural or synthetic bioactive compounds. In addition to the capacity of these chemical motifs to impact the physicochemical properties of a molecule of interest, the well-established reactivity of alkynes makes them ...
Jan Van Herle, Hossein Pourrahmani