6533b82bfe1ef96bd128d4d2

RESEARCH PRODUCT

Enantioselektive Trifluoracetylierung mit Hilfe chiraler Polyamide

subject

description

(S)-Poly(2-aminobutyric acid) (1) [(S)-poly(imino-1-methyl-3-oxotrimethylene)] was transformed into its N-trifluoroacetyl derivative 4. The IR spectra and the circular dichroism of both substances were compared. In addition, (S)-poly[N-(1-phenylethyl)acrylamide] (2) ((S)-poly-[1-(1-phenylethylaminocarbonyl)ethylene]) was trifluoroacetylated leading to polymer 5. 4 was found to react as trifluoroacetylating agent with L-1-phenylethylamine (L-3) twice as fast as it reacts with D-3. Accordingly, the reaction of 4 with D,L-3 leads preferentially to the L-form of N-(1-phenylethyl)trifluoroacetamide with optical yields up to 6%. The reaction of 5 with D,L-3 affords the D-form of N-(1-phenylethyl)trifluorcacetamide with optical yields up to 13%.