The stereochemistry of proton removal in the formation of π-allyl palladium complexes from steroid 4-En-3-ones

Abstract

Reaction of (6β-²H)- and (6α-²H)-cholest-4-en-3-one with palladium(II) chloride in dry tetrahydro- furan gives the α-4-6-η-PdCl compound with highly stereoselective loss of the 6β deuterium or proton. The mechanistic implications of this stereoselectivity are discussed.