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Selective 1,2‐addition of organocerium(III) reagents to α,β‐unsaturated carbonyl compounds
Author(s) -
Imamoto Tsuneo,
Sugiura Yasushi
Publication year - 1989
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610020202
Subject(s) - chemistry , reagent , ethylenedioxy , allylic rearrangement , addition reaction , medicinal chemistry , organic chemistry , computational chemistry , photochemistry , catalysis , alkyl
Organocerium(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.