Convenient access to functionalized vinylcyclopentenols from alkynyloxiranes.
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.
Wang
Letian
L
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Maddess
Matthew L
ML
Lautens
Mark
M
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*
D000438:Alcohols; D000480:Alkynes; D003517:Cyclopentanes; D007202:Indicators and Reagents; D014753:Vinyl Compounds; D005027:Ethylene Oxide