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

• Published in: Acta Chemica Scandinavica
• Main Authors: Mattson, A., Orrenius, C., Ohrner, N., Unelius, C. R., Hult, K., Norin, T.
• Format: Article in Journal/Newspaper
• Language: English
• Published: KTH, Sweden 1996
• Subjects: ethyl-octanoate; transesterification; acid; Natural Sciences; Naturvetenskap; Antarc*; Antarctica
• Online Access: http://urn.kb.se/resolve?urn=urn:nbn:se:lnu:diva-14105; https://doi.org/10.3891/acta.chem.scand.50-0918

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.