A SIMPLE ONE-POT SYNTHESIS OF ALPHA-TRIFLUOROMETHYL-SUBSTITUTED ENAMINES BY C-TRIFLUOROMETHYLATION OF DIALKYLAMIDES WITH P(NET(2))(3)/CF3BR

Dialkylamides of the general formula R(3)R(2)NC(O)CH(2)R(1), and Me-N-C(O)-CH2-(CH2)(n)-CH2, n=1-3, react with the reagent combination P(NEt(2))(3)/CF3Br in the presence of BCl3 to give alpha-trifluoromethyl enamines R(3)R(2)N-C(CF3)=CHR(1), R(1)=H, R(2)=R(3)=Me (I), Et(II), Pr-i(III); R(2)=(n)Bu, R(3)=Me(IV); R(1)=R(2)=R(3)=Me(Va/b); Me-N-C(CF3)=CH-(CH2)(n)-CH2, n=1 (VI), 2 (VII) and 3 (VIII) in yields of 25%-36%. Hydrolysis of VI by hydrochloric acid yielded the salt [Me-NH-C(CF3)(OH)-CH2-CH2-CH2]Cl-+(-) (IX), the deprotonation of which with NaOH gave the 2-hydroxypyrrolidine Me-N-C(CF3)(OH)-CH2-CH2-CH2 (X). The novel compounds have been characterized by elemental analyses, multinuclear NMR, IR and mass spectroscopy.