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South African Journal of Chemistry

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The Evaluation of Novel Camphor-derived Pyridyl Ligands as Catalysts in the Asymmetric Diels-Alder Reaction of Cyclopentadiene with 3-Acryloyl-2-oxazolidinone

GA Boyle, T Govender, HG Kruger, T Naicker, GEM Maguire

Abstract


A series of camphor-derived pyridyl ligands were evaluated in the Diels-Alder reaction of 3-acryloyl-2-oxazolidinone 1 with cyclopentadiene 2. High yields with good endo:exo selectivity, but only moderate enantioselectivities (43 % ee), were obtained. The structures of the copper (II) complexes of the ligands were calculated using ONIOM density functional theory and the results suggest that chiral induction to the alkene functional group is indeed lacking. This explains the moderate experimental selectivities obtained.

Keywords: Camphor ligands, asymmetric catalysis, Diels-Alder cycloaddition, computational modelling

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