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RUTHENIUM-CATALYZED TANDEM OLEFIN MIGRATION-ALDOL AND MANNICH-TYPE REACTIONS IN IONIC LIQUID.
Yang, X. F., M. Wang, R S. Varma*, AND C. J. Li. RUTHENIUM-CATALYZED TANDEM OLEFIN MIGRATION-ALDOL AND MANNICH-TYPE REACTIONS IN IONIC LIQUID. Bourbigon, H.O., Chauvin, Y. (ed.), JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL. Elsevier Online, New York, NY, 214(1):147-154, (2004).
In the presence of a catalytic amount of RuCl2(PPh3)3, a cross-coupling of 3-buten-2-ol with aldehydes and imines was developed via a tandem olefin migration--aldol--Mannich reaction in bmim[PF6]. With In(OAc)3 as a co-catalyst, a-vinylbenzyl alcohol and aldehydes underwent similar coupling reactions. Compared with aqueous and other organic solvents, complementary diastereoselectivity was observed with ionic liquid as the solvent. The ionic liquid/catalyst system could be reused at least five times without loss of activity.