Chiral pyridine imidazolines from C1-symmetric diamines: Synthesis, arene ruthenium complexes and application as asymmetric catalysis for Diels-Alder reactions |
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Authors: | Adam J Davenport John Fawcett David R Russell |
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Institution: | Department of Chemistry, University of Leicester, Leicester LE1 7RH, United Kingdom |
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Abstract: | Condensation of mono N-substituted chiral ethylenediamines and pyridine-2-methoxyimidate gives new chiral pyridine imidazolines (1a-c). These react with RuCl2(mes)]2 (mes = 1,3,5-trimethyl benzene) in the presence of NaSbF6 to give complexes RuCl(L)(mes)]SbF6] (5a-c) which after treatment with AgSbF6 are enantioselective catalysts for the Diels-Alder reaction of methacrolein and cyclopentadiene. The imidazoline catalysts are less selective than the corresponding oxazoline ones. Compounds 1a, 5b and 5c have been characterised by X-ray crystallography. |
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Keywords: | Chiral Half-sandwich Imidazoline Asymmetric catalysis |
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