Abstract
Abstract The reactions of α-imino ketones, derived from arylglyoxals, with (trifluoromethyl)trimethylsilane (CF 3 SiMe 3 ) in DME solution, in the presence of catalytic amount of CsF, at room temperature, yield O-silylated β-imino alcohols in the chemoselective manner. Subsequent reduction of these products with NaBH 4 in ethanolic solution leads to the corresponding β-(N-alkyl)amino-α-trifluoromethyl alcohols in good to excellent yields. Trifluoromethylation of enantiomerically pure α-imino ketones (with Ar = Ph or p -MeOC 6 H 4 ), bearing as a chiral auxiliary the PhCH(Me) group attached to the nitrogen atom, yields mixtures of diastereomeric products in the ratio of ca. 3:2.
Published Version
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