Chemoselective Strain Release of Bicyclo[1.1.1]pent-1-yl Alcohols

Abstract The chemoselective C–C bond cleavage of bicyclo[1.1.1]pent-1-yl alcohols (BCP-OHs) was examined. Highly ring-strained BCP-OHs were found to be particularly reactive, delivering cyclobutanone derivatives through a base-mediated single C–C bond cleavage or α,β-unsaturated ketones by palladium-catalyzed dual C–C bond cleavage.