Design and synthesis of enantiopure 1-[1(S)-(2-pyridyl)alkyl]-2(R)-isopropylaziridines, new ligands for asymmetric catalysis |
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Authors: | Katia Fiore Gianluca Martelli Magda Monari Diego Savoia |
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Affiliation: | Dipartimento di Chimica ‘G. Ciamician’, Università di Bologna, via Selmi 2, 40126 Bologna, Italy |
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Abstract: | Enantiopure 1-(2-pyridyl)alkyl aziridines were designed as bidentate ligands for asymmetric catalysis. Their synthesis involved the addition of organometallic reagents to the imine prepared from 2-pyridinealdehyde and an enantiopure β-aminoalcohol, followed by cyclisation of the β-aminoalcohol moiety to the aziridine ring. Two such ligands (N–N)* were prepared from (S)-valinol and converted to the complexes (η3-allyl)(N–N)*Pd+SbF6−, one of which was characterised by X-ray crystallography. Modest enantioselectivities were achieved in a representative Pd-catalysed allylic substitution reaction. |
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