Synthesis of tetrahydropyrans from propargyl alcohols and 1,1-cyclopropanediesters: a one-pot ring-opening/Conia-ene protocol.
Lewis acid catalyzed ring opening of 1,1-cyclopropanediesters by the hydroxyl group of a propargyl alcohol sets up a subsequent Conia-ene cyclization to afford substituted tetrahydropyrans in a one-pot, high-yielding procedure.
Leduc
Andrew B
AB
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Lebold
Terry P
TP
Kerr
Michael A
MA
D000480:Alkynes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D020005:Propanols / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis*
D000480:Alkynes; D020005:Propanols; D011714:Pyrans; C028255:propargyl alcohol