Palladium complexes of phosphinamine ligands in the intramolecular asymmetric Heck reaction |
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Authors: | Denis Kiely |
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Institution: | Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, Department of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland |
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Abstract: | The synthesis of two novel cyclisation substrates for the asymmetric intramolecular Heck reaction is reported. Their cyclisation, in addition to a known substrate for cis-decalin formation, were tested with palladium complexes of BINAP and heterobidentate oxazoline-containing ligands. In general BINAP provides a more active catalyst system for the range of substrates tested although excellent enantioselectivities of up to 85% were obtained with the P,N ligands studied. A trend was noted whereby the t-leucine-derived oxazoline ligands were more reactive and enantioselective than the valine-derived analogues. Similarly, the diphenylphosphinoferrocenyloxazoline ligands were more reactive and selective than the corresponding diphenylphosphinophenyloxazoline ligands. |
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Keywords: | Palladium Asymmetric catalysis Intramolecular Heck reaction Phosphinamine ligands |
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