Stereoselectivity in the Hydrosilylation of 2-Alkyl-substituted Cyclopentanones and Cyclohexanones Catalyzed by Chlorotris(triphenylphosphine)rhodium Complex

Abstract

The stereoselectivity in the rhodium(I)-catalyzed reduction of 2-alkyl-substituted cyclopentanones and cyclohexanones with organosilanes was investigated. Relative amount of the more stable alcohol increased with bulkiness of organosilanes used, and the more bulkiness of 2-alkyl substituents produced the larger percentage of less stable of the two possible alcohols. The results were compared with those of the reduction by boranes and those of hydrogenation over platinum catalyst.