Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides |
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Authors: | Hodgson David M Glen Rebecca Grant Guy H Redgrave Alison J |
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Institution: | Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, UK. david.hodgson@chem.ox.ac.uk |
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Abstract: | An evaluation of alpha-aryl-alpha-diazodiones in tandem carbonyl ylide formation-enantioselective 3 + 2]-cycloaddition reactions is described. Such substrates were designed to allow investigation of the electronic characteristics of the dipole upon asymmetric induction. Intramolecular cycloadditions (with a tethered alkene dipolarophile) were found to occur in good to quantitative yields, with a difference in ee exhibited by the two electronically different diazodiones 8 and 9. Intermolecular cycloadditions using diazodiones 12 and 13 with DMAD and arylacetylenes 16-18 again demonstrated that electronics play a key role in determining the outcome of the cycloaddition reactions. Enantioselectivities of up to 76% were observed. |
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