Palladium-catalyzed reactions of cyclopropanols bearing oxazoline directing group

Cyclopropanols bearing oxazoline directing group were investigated in palladium-catalyzed reactions. When the directing group and cyclopropanol unit were bonded through two- or three-carbon spacer, formation of unusual products was observed. Oxidative ring opening proceeded with uncommon regioselectivity providing linear enones as main products. The reaction of such cyclopropanols with aryl iodides and silver acetate furnished diarylated alpha-methylene ketones, which cannot be obtained from cyclopropanols lacking oxazoline ring under the same conditions. (C) 2018 Elsevier Ltd. All rights reserved.