Zn(II)/amine-catalyzed coupling reaction of alkylidenemalonates with propargyl alcohol: a one-pot synthesis of methylenetetrahydrofurans.
[reaction: see text] A metal-catalyzed tandem 1,4-addition/cyclization between propargyl alcohol and a Michael acceptor, such as alkylidene malonate, has been developed. In the presence of catalytic amounts of zinc triflate [Zn(OTf)(2)] and triethylamine (Et(3)N), various 2-alkylidene-1,3-dicarbonyl compounds reacted with propargyl alcohol to give 3- or 4-methylene tetrahydrofurans in excellent yields.
Nakamura
Masaharu
M
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Liang
Chungen
C
Nakamura
Eiichi
E
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D008314:Malonates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D000480:Alkynes; D000588:Amines; D005663:Furans; D008314:Malonates; D009942:Organometallic Compounds; D020005:Propanols; C028255:propargyl alcohol; D015032:Zinc