Synthesis of a Schiff’s base chiral ligand with a trifluoromethyl carbinol moiety

A Schiff’s base ligand with a trifluoromethyl carbinol moiety was synthesized, and a structure of the active complex for asymmetric induction on the reaction of diethylzinc with aldehydes is proposed.

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(S,E)-2-((2-(2,2,2-Trifluoro-1-hydroxyethyl)phenylimino)methyl)phenolC15H12F3NO2[α]D20.5=-159.5 (c 1.10, CHCl3)

(S)-1-(2-Aminophenyl)-2,2,2-trifluoroethanolC8H8F3NO[α]D20.5=+32.7 (c 1.40, CH3OH)