Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides
| dc.contributor.author | Hodgson, David M. | en_GB |
| dc.contributor.author | Glen, Rebecca | en_GB |
| dc.contributor.author | Grant, Guy H. | en_GB |
| dc.contributor.author | Redgrave, Alison J. | en_GB |
| dc.date.accessioned | 2013-09-23T12:33:24Z | |
| dc.date.available | 2013-09-23T12:33:24Z | |
| dc.date.issued | 2003 | |
| dc.identifier.citation | Hodgson, 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 | en_GB |
| dc.identifier.issn | 0022-3263 | |
| dc.identifier.issn | 1520-6904 | |
| dc.identifier.doi | 10.1021/jo026307t | |
| dc.identifier.uri | http://hdl.handle.net/10547/302107 | |
| dc.description.abstract | An 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. | |
| dc.language.iso | en | en |
| dc.publisher | American Chemical Society | en_GB |
| dc.relation.url | http://pubs.acs.org/doi/abs/10.1021/jo026307t | en_GB |
| dc.rights | Archived with thanks to The Journal of Organic Chemistry | en_GB |
| dc.title | Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides | en |
| dc.type | Article | en |
| dc.contributor.department | University of Oxford | en_GB |
| dc.contributor.department | GlaxoSmithKline Medicines Research Centre | en_GB |
| dc.identifier.journal | The Journal of Organic Chemistry | en_GB |
| html.description.abstract | An 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. |