Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides

2.50
Hdl Handle:
http://hdl.handle.net/10547/302107
Title:
Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides
Authors:
Hodgson, David M.; Glen, Rebecca; Grant, Guy H.; Redgrave, Alison J.
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.
Affiliation:
University of Oxford; GlaxoSmithKline Medicines Research Centre
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
Publisher:
American Chemical Society
Journal:
The Journal of Organic Chemistry
Issue Date:
2003
URI:
http://hdl.handle.net/10547/302107
DOI:
10.1021/jo026307t
Additional Links:
http://pubs.acs.org/doi/abs/10.1021/jo026307t
Type:
Article
Language:
en
ISSN:
0022-3263; 1520-6904
Appears in Collections:
Cell and Cryobiology Research Group

Full metadata record

DC FieldValue Language
dc.contributor.authorHodgson, David M.en_GB
dc.contributor.authorGlen, Rebeccaen_GB
dc.contributor.authorGrant, Guy H.en_GB
dc.contributor.authorRedgrave, Alison J.en_GB
dc.date.accessioned2013-09-23T12:33:24Z-
dc.date.available2013-09-23T12:33:24Z-
dc.date.issued2003-
dc.identifier.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.581-586en_GB
dc.identifier.issn0022-3263-
dc.identifier.issn1520-6904-
dc.identifier.doi10.1021/jo026307t-
dc.identifier.urihttp://hdl.handle.net/10547/302107-
dc.description.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.en_GB
dc.language.isoenen
dc.publisherAmerican Chemical Societyen_GB
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/jo026307ten_GB
dc.rightsArchived with thanks to The Journal of Organic Chemistryen_GB
dc.titleCatalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylidesen
dc.typeArticleen
dc.contributor.departmentUniversity of Oxforden_GB
dc.contributor.departmentGlaxoSmithKline Medicines Research Centreen_GB
dc.identifier.journalThe Journal of Organic Chemistryen_GB
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