Fourteen Salen ligands derived from 1,2-cyclohexanediamine, 1,2-diphenylethylenediamine or 1,2-phenylenediamine were synthesized and also used as catalysts to the enantioselective ring-opening reaction of cyclohexene oxide with phenyl lithium. Results indicated that enantioselectivity was greatly influenced by the structure of the chiral diamine moiety and substituents at 3,3'-positions in benzene ring. The enantioselective ring-opening reaction of cyclohexene oxide with phenyl lithium was also investigated via catalysis by some Ga(Salen) compounds derived from Salen and Me₃Ga, and better yields and enantioselectivities were afforded than those of reaction directly catalyzed by Salen. Enantioenriched trans-phenylcyclo-hexanol was obtained in up to 73% ee when Ga(Salen) 15 was used as the catalyst.

Key words: Ga(Salen), Salen, phenyl lithium, asymmetric catalysis, cyclohexene oxide