New chiral auxiliaries derived from (S)-α-phenylethylamine as chiral solvating agents for carboxylic acids

The two new diastereoisomeric chiral auxiliaries 1a and 1b were synthesized conveniently and effectively. 1H NMR was employed to investigate their chiral recognition ability. Compared with (S)-PEA, these new chiral auxiliaries exhibited better enantioselectivity towards the carboxylic acids we had chosen.

The two new diastereoisomeric chiral auxiliaries 1a and 1b were synthesized conveniently and effectively. 1H NMR was employed to investigate their chiral recognition ability. Compared with (S)-PEA, these new chiral auxiliaries exhibited better enantioselectivity towards the carboxylic acids we had chosen.Figure optionsDownload as PowerPoint slide

N,N,4-Trimethyl-2-[(S)-{[(S)-1-phenylethyl]amino}(1-naphthyl)methyl]anilineC28H30N2Ee = 100%[α]D20=+113.2 (c 1.55, CHCl3)Source of chirality: (S)-α-phenylethylamineAbsolute configuration: (S,S)

N,N,4-Trimethyl-2-[(R)-{[(S)-1-phenylethyl]amino}(1-naphthyl)methyl]anilineC28H30N2Ee = 100%[α]D20=-12.6 (c 1.35, CHCl3)Source of chirality: (S)-α-phenylethylamineAbsolute configuration: (R,S)