Selective 1,2‐addition of organocerium(III) reagents to α,β‐unsaturated carbonyl compounds

Abstract

AbstractOrganocerium(III) reagents reacted with α,β‐unsaturated carbonyl compounds to give 1, 2‐addition products (allylic alcohols) in good to high yields. The reaction was studied from a mechanistic point of view by the use of (E)‐ and (Z)‐1‐(4′‐methoxyphenyl)‐3‐phenyl‐2‐propen‐1‐ones and 4,4‐ethylenedioxy‐2,6‐dimethyl‐2,5‐cyclohexadienone as the probe compounds. A polar pathway was suggested for the reaction with the former enones. On the other hand, the operability of single electron transfer processes was demonstrated in the reaction with the latter probe compound.