Abstract
Coordinated 1-phenyl-3,4-dimethylphosphole in the chiral complex chloro{( S)-1-[1-(dimethylamino)ethyl]naphthyl- C 2,N }[1-phenyl-3,4-dimethylphosphole- P]palladium behaves as an activated cyclic diene in the inter-molecular Diels–Alder reaction with 1-methyl-2-vinylpyrrole to give a pair of diastereomeric P-chiral endo-cycloadducts. The diastereomeric palladium complexes could be separated by fractional crystallization and the enantiomerically pure phosphanorbornene ligands could be liberated individually from the complexes by treatment with potassium cyanide. In contrast, the [4+2] cycloaddition reaction did not occurred under similar conditions when the chloro ligand in the phosphole complex was replaced with a perchlorato ligand.
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