Ruthenium-catalyzed isomerization of homoallylic alcohols in water

Through the catalysts of RuCl2(PPh3)(3), the functional groups of homoallylic alcohols are repositioned to give allylic alcohols with controlled regioselectivity. The reaction proceeds most efficiently in an aqueous media. The selectivity in product formation is affected by the reaction temperature and the amount of the catalyst being used. A higher reaction temperature and the use of a smaller amount of the catalyst are preferable for the formation of allylic alcohols. The reaction process was postulated as a tandem olefin migration-allylic rearrangement. Under the same reaction conditions, the functional groups of allylic alcohols undergo allylic rearrangements. (C) 1998 Elsevier Science Ltd. All rights reserved.