Improvement of the asymmetry-inducing ability of a trifluoromethylated amino alcohol by electron donation to a CF3 group

An improvement in the ‘net asymmetric-inducing ability’ of a trifluoromethylated amino alcohol ligand by influencing the CF3 group with an electron donating 2-propyl group is reported.

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(2S)-1,1,1-Trifluoro-2-methyl-3-(N-piperidino)-2-propanolC9H16F3NO[α]D25=+9.9 (c 0.0142, CHCl3)Source of chirality: enantiomerically pure epoxideAbsolute configuration: (2S)

(2S)-2-Benzoyl-1,1,1-trifluoro-2-methyl-3-(N-piperidino)propaneC16H20F3NO2[α]D25=+0.4 (c 0.0115, CHCl3)Source of chirality: stereospecific synthesisAbsolute configuration: (2S)

(2S)-1,1,1-Trifluoro-3-methyl-2-(N-piperidinomethyl)-2,3-butanediolC11H20F3NO2[α]D25=-3.3 (c 0.0103, CHCl3)Source of chirality: enantiomerically pure epoxideAbsolute configuration: (2S)

(2S)-1,1,1-Trifluoro-3-methyl-2-(N-piperidinomethyl)-3-buten-2-olC11H18F3NO[α]D25=-0.6 (c 0.0138, CHCl3)Source of chirality: stereospecific synthesisAbsolute configuration: (2S)

(2S)-1,1,1-Trifluoro-3-methyl-2-(N-piperidinomethyl)-2-butanolC11H20F3NO[α]D25=+2.8 (c 0.0112, CHCl3)Source of chirality: stereospecific synthesisAbsolute configuration: (2S)

(2S)-2-Benzoyl-1,1,1-trifluoro-3-methyl-2-(N-piperidinomethyl)butaneC18H24F3NO2[α]D25=+5.3 (c 0.0119, CHCl3)Source of chirality: stereospecific synthesisAbsolute configuration: (2S)