title: Convenient access to functionalized vinylcyclopentenols from alkynyloxiranes.
abstract: Beta,gamma-alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)3 or BF3.OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
authors.forename: Letian
authors.initials: L
authors.lastname: Wang
authors.forename: Matthew L
authors.initials: ML
authors.lastname: Maddess
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000138:chemical synthesis*; D005027:Ethylene Oxide / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D017403:In Situ Hybridization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D017550:Spectroscopy, Fourier Transform Infrared; D014753:Vinyl Compounds / Q000138:chemical synthesis*
chemical_list: D000438:Alcohols; D000480:Alkynes; D003517:Cyclopentanes; D007202:Indicators and Reagents; D014753:Vinyl Compounds; D005027:Ethylene Oxide