Asymmetric allylic substitution of cycloalkenyl esters in water with an amphiphilic resin&-supported chiral palladium complex*
Yasuhiro Uozumi
Institute for Molecular Science (IMS), Myodaiji, Okazaki, Aichi 444-8787, Japan
Abstract: A novel homochiral phosphine ligand, (3R,9aS)[2-aryl-3-(2-diphenylphosphino)phenyl]tetrahydro-1H-imidazo[1,5-a]indole-1-one, was designed, prepared, and anchored onto an amphiphilic polystyrene-poly(ethylene glycol) copolymer (PS-PEG) resin. Catalytic asymmetric substitution of a racemic mixture of cycloalkenyl esters with carbon, nitrogen, and oxygen nucleophiles was achieved in water as the single reaction medium under heterogeneous conditions by using the PS-PEG resin-supported palladium-imidazoindole phosphine complex to give optically active substituted cycloalkenes with up to 99 % ee.
Keywords: palladium; asymmetric; aqueous medium; catalysis; polymer support; immobilization.
*Paper based on a presentation at the 12th International Conference on Polymers and Organic Chemistry 2006 (POC'06), 2-7 July 2006, Okazaki, Japan. Other presentations are published in this issue, pp. 1471-1582.