title: Intramolecular cycloaddition reactions of cis-1,2-dihydrocatechol derivatives incorporating C3-tethered diazoketones, nitrile oxides, and azides: stereocontrolled routes to enantiomerically pure spiro[5.5]undecanes and related systems.
abstract: A series of enantiomerically pure cis-1,2-dihydrocatechol derivatives incorporating C3-tethered diazoketone, nitrile oxide, or azide residues has been prepared from the precursor iodide 7 using Negishi cross-coupling reactions. Such derivatives, including diazoketone 12, participate in regio- and stereo-selective intramolecular cycloaddition reactions to give adducts, for example, 15, that are readily elaborated to spiro[5.5]undecanes such as 18.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia.
authors.forename: Tristan A
authors.initials: TA
authors.lastname: Reekie
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D001386:Azides; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007659:Ketones; D009570:Nitriles; D010087:Oxides; D013141:Spiro Compounds; C022884:undecane