Please use this identifier to cite or link to this item: https://doi.org/10.1016/S0957-4166(98)00012-3
Title: 1-methyl-2-vinylpyrrole and 1-phenyl-3,4-dimethylphosphole: Their coordination chemistries and reactivities in a chiral palladium complex promoted asymmetric Diels-Alder reaction
Authors: Loh, S.-K.
Vittal, J.J. 
Leung, P.-H. 
Issue Date: 13-Feb-1998
Citation: Loh, S.-K., Vittal, J.J., Leung, P.-H. (1998-02-13). 1-methyl-2-vinylpyrrole and 1-phenyl-3,4-dimethylphosphole: Their coordination chemistries and reactivities in a chiral palladium complex promoted asymmetric Diels-Alder reaction. Tetrahedron Asymmetry 9 (3) : 423-428. ScholarBank@NUS Repository. https://doi.org/10.1016/S0957-4166(98)00012-3
Abstract: Coordinated 1-phenyl-3,4-dimethylphosphole in the chiral complex chloro{(S)-1-[1-(dimethylamino)ethyl]naphthylC2,N}[1-phenyl-3,4- dimethylphosphole-P]palladium behaves as an activated cyclic diene in the intermolecular Diels-Alder reaction with 1-methyl-2-vinylpyrrole to give a pair of diastereomeric P-chiral endocycloadducts. 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.
Source Title: Tetrahedron Asymmetry
URI: http://scholarbank.nus.edu.sg/handle/10635/92906
ISSN: 09574166
DOI: 10.1016/S0957-4166(98)00012-3
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