Diastereoselectivity in the heterogeneous hydrogenation reactions of phosphorous substituted olefins

Phosphorous substituted methylenecyclohexane olefins show enhanced diastereoselectivity in heterogeneous hydrogenation reactions using Pd/C. A model system derived from 4-t-butylcyclohexanone was used to explore the effects of solvent polarity and catalyst on the reduction reaction. It was found that olefins hydrogenated with catalytic Pd/C in polar solvents afford the highest diastereoselectivities (>15:1). (C) 1997 Elsevier Science Ltd.