Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides
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AbstractAn evaluation of α-aryl-α-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.
CitationHodgson, D.M., Glen, R., Grant, G.H. and Redgrave, A.J. (2003) 'Catalytic Enantioselective [3 + 2]-Cycloadditions of Diazoketone-Derived Aryl-Substituted Carbonyl Ylides', The Journal of Organic Chemistry, 68(2), pp.581-586
PublisherAmerican Chemical Society
JournalThe Journal of Organic Chemistry