Asymmetric Reduction of Prochiral α-Halo Ketones with B-3-Pinanyl-9-borabicyclononane

Article abstract of DOI:10.1021/jo00158a046

B-3-Pinanyl-9-borabicyclo<3.3.1>nonane reduces aryl α-haloalkyl ketones to the corresponding halohydrins in nearly quantitative chemical yield and high optical induction.This reagent yields somewhat lower optical induction in the case of the aliphatic analogue, 1-bromo-3-methyl-2-butanone.The halohydrins can be converted to the corresponding chiral epoxides or dehalogenated to the parent alcohol with retention of optical activity.