title: Multicatalytic synthesis of complex tetrahydrofurans involving bismuth(III) triflate catalyzed intramolecular hydroalkoxylation of unactivated olefins.
abstract: A multicatalytic synthesis of complex tetrahydrofurans has been developed involving a Bi(OTf)(3)-catalyzed nucleophilic addition/hydroalkoxylation sequence. Complex tetrahydrofuranyl products may be formed rapidly in high yield and with good diastereoselectivity. The demonstrated scope of hydroalkoxylation has also been expanded to include substrates bearing useful functional handles including carboxylate ester, olefin, nitrile, and nitro groups.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, USA.
authors.forename: Brendan D
authors.initials: BD
authors.lastname: Kelly
authors.forename: Julia M
authors.initials: JM
authors.lastname: Allen
authors.forename: Rachel E
authors.initials: RE
authors.lastname: Tundel
authors.forename: Tristan H
authors.initials: TH
authors.lastname: Lambert
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000475:Alkenes; D005663:Furans; D008698:Mesylates; C445789:Bi(OTf)3