Kinetic resolution of chiral auxiliaries with C-2-symmetry by lipase-catalyzed alcoholysis and aminolysis

Three cyclic diols, 1,2-cyclohexanediol (1), 1,3-cyclohexanediol (2), and 1,3-cyclopentanediol (3), two acyclic unsaturated diols, 1,5-hexadiene-3,4-diol (4) and 1,7-octadiyne-3,6-diol (5), and a cyclic diamine, 1,2-cyclohexanediamine (6), have been kinetically resolved in alcoholysis and aminolysis reactions, catalyzed by Candida antarctica component B lipase, using S-ethyl thiooctanoate or ethyl octanoate as acyl donors. Acceptable stereoselectivity was achieved in most cases.