Bong Chan Kim

Nucleophilic Fluorination of Triflates by Tetrabutylammonium Bifluoride

Careful examination of nucleophilicity, basicity, and leaving group ability led us to discover the nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride, which provides excellent yields with minimal formation of elimination-derived side products. Primary hydroxyl groups as well as secondary hydroxyl groups in acyclic chains or in five-membered rings are excellent substrates, whereas benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.

Highly diastereoselective reduction of enantiomerically pure aziridino ketones

Abstract Various enantiomerically pure aziridino ketones were prepared from the corresponding secondary alcohols by Swern oxidation. Those configurationally stable α-amino ketones were stereoselectively reduced by L-Selectride® to provide the corresponding alcohol with high diastereoselectivities and chemical yields.