UNUSUAL HIGH REACTIVITIES OF 5α- AND 5β-CHOLESTAN-3-ONES IN THE HYDROGENATION CATALYZED BY PALLADIUM. EVIDENCE FOR AN ATTRACTIVE INTERACTION OF THE STEROID α-FACE WITH PALLADIUM

Article abstract of DOI:10.1246/cl.1980.1239

5α- And 5β-cholestan-3-ones are 30 and 17 times as reactive as 4-t-butylcyclohexanone in Pd catalyzed competitive hydrogenation in t-BuOH.The high reactivity of the steroid ketones and unusual hydrogenation stereochemistry on Pd have been explained on the basis of an attractive interaction of the steroid α-face with Pd.