title: Rh(I)-catalyzed ring-opening of hetaryne-furan Diels-Alder adducts: rapid access to stereochemically defined heterocyclic scaffolds.
abstract: Probing the nucleophilic ring-opening of various bicyclic [2.2.1] hetaryne-furan Diels-Alder adducts revealed that efficient reactivity could be observed with heteroatom nucleophiles by using a cationic Rh(I) complex in combination with a chiral Josiphos-type phosphine ligand. Remarkably, this catalyst system was not impeded by the incorporation of a heteroatom into the substrate. Racemic materials afforded separable mixtures of enantioenriched regioisomers, indicating that strong reagent control is operative.
authors.affiliation: Department of Chemistry, University of Toronto, Toronto, Ontario, Canada, M5S 3H6.
authors.forename: Trung D
authors.initials: TD
authors.lastname: Nguyen
authors.forename: Robert
authors.initials: R
authors.lastname: Webster
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D012238:Rhodium