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Synthesis 2003(10): 1574-1578
DOI: 10.1055/s-2003-40513
DOI: 10.1055/s-2003-40513
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
A Novel Base-Catalyzed Stereoselective Synthesis of Trifluoromethylated Dienedinitriles
Weitere Informationen
Publikationsverlauf
Received
31 March 2003
Publikationsdatum:
08. Juli 2003 (online)


Abstract
The trifluoromethylated γ-cyano-β,γ-unsaturated nitrile 4 was prepared by the reaction of bromo(cyanomethyl)zinc with trifluoroacylated phosphonate 3 in 67% yield (E:Z = 60:40). The E- and Z-isomers obtained were easily separated by column chromatography. Treatment of a catalytic amount of t-BuOK (20 mol%) with a mixture of (Z)-4 and N-toluenesulfonylimines 5 gave trifluoromethylated dienedinitriles 6 in 68-83% yields.
Key words
trifluoromethylated dienedinitriles - γ-cyano-β,γ-unsaturated nitrile - trifluoroacylated phosphonate - organozinc reagent - stereoselective synthesis