Abstract
[reaction: see text] Catalytic asymmetric allylic amination of cycloalkenyl carbonates (methyl cyclohexen-2-yl carbonate, methyl cyclohepten-2-yl carbonate, methyl 5-methoxycarbonylcyclohexen-2-yl carbonate, methyl cyclohexenyl carbonate, tert-butyl 5-methoxycarbonyloxy-1,2,5,6-tetrahydropyridinedicarboxylate) with dibenzylamines ((C6H5CH2)2NH, (C6H5CH2)(4-CH3OC6H4CH2)NH, (4-CH3OC6H4CH2)2NH) was achieved in water under heterogeneous conditions by use of a palladium complex of (3R,9aS)-3-[2-(diphenylphosphino)phenyl]-2-phenyltetrahydro-1H-imidazo[1,5-a]indole-1-one anchored on polystyrene-poly(ethylene glycol) copolymer resin to give the corresponding cycloalkenylamines with high enantiomeric selectivity (90-98% ee).
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