Tetrahedron

Carbonyl-yne reactions of 3, 3, 3-trifluoropyruvates

AS Golubev, NN Sergeeva, L Hennig, AF Kolomiets…

Index: Golubev, Alexander S.; Sergeeva, Natalia N.; Hennig, Lothar; Kolomiets, Alexey F.; Burger, Klaus Tetrahedron, 2003 , vol. 59, # 9 p. 1389 - 1394

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Citation Number: 18

Abstract

An efficient synthesis of trifluoromethyl-containing 2, 3-allenols via carbonyl-yne reaction of 3, 3, 3-trifluoropyruvates with acetylenes is described. In the presence of MgBr2· Et2O the reaction of methyl trifluoropyruvate with hex-1-yne proceeds diastereoselectively. Trifluoromethyl-substituted 2, 3-allenols can be stereoselectively transformed into trifluoromethyl-substituted 2, 5-dihydrofurans on treatment with AgNO3.