FACILE SYNTHESIS OF TRIFLUOROMETHYL CARBINOLS AND TRIFLUOROMETHYL-ALPHA,BETA-UNSATURATED KETONES FROM THE NEW CF3CHO SYNTHETIC EQUIVALENT, 1,1-BIS(DIMETHYLAMINO)-2,2,2-TRIFRUOROETHANE
Yl. Xu et Wr. Dolbier, FACILE SYNTHESIS OF TRIFLUOROMETHYL CARBINOLS AND TRIFLUOROMETHYL-ALPHA,BETA-UNSATURATED KETONES FROM THE NEW CF3CHO SYNTHETIC EQUIVALENT, 1,1-BIS(DIMETHYLAMINO)-2,2,2-TRIFRUOROETHANE, Tetrahedron letters, 39(50), 1998, pp. 9151-9154
1,1-Bis(dimethylamino)-2,2,2-trifluoroethane is an excellent synthetic
building-block replacement for trifluoroacetaldehyde in condensation
reactions with ketones using 36% aqueous HCl catalysis. Moderate to go
od yields (43-68%) of trifluoromethyl carbinols are obtained with symm
etric and unsymmetric methyl ketones, with the latter undergoing react
ion mainly at the methyl group. Its reactions with silyl enol ethers u
nder anhydrous conditions, catalyzed by ZnI2, lead directly to trifluo
romethyl-alpha,beta-unsaturated ketones. (C) 1998 Elsevier Science Ltd
. All rights reserved.