Ruthenium-catalyzed processes: Multi-faceted reactivity of propargylic alcohols with bicyclic alkenes

ORGN 274

Karine Villeneuve, kvillene@uoguelph.ca and William Tam, wtam@uoguelph.ca. Department of Chemistry, University of Guelph, Guelph, ON N1G 2W1, Canada
Propargylic alcohols have been utilized in various ruthenium-catalyzed reactions including dimerization, cyclopropanation and Alder-ene reactions. Recently, our group reported a diastereoselective version of the ruthenium-catalyzed [2+2] cycloaddition between chiral propargylic alcohol and bicyclic alkenes. During the course of studying the scope of this reaction, unprecedented reactivity pathways were discovered. It was found that the size of the ring formed could be selected by altering the reaction components (alkene, alkynol) and conditions (solvent, ruthenium catalyst). Our preliminary mechanistic studies will also be discussed.