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...

Full description

Saved in:
Bibliographic Details
Published inActa chemica Scandinavica (Copenhagen. 1989) Vol. 50; no. 10; pp. 918 - 921
Main Authors Mattson, A, Orrenius, C, Ohrner, N, Unelius, CR, Hult, K, Norin, T
Format Journal Article
LanguageEnglish
Published COPENHAGEN Wiley 01.10.1996
Subjects
Biochemistry & Molecular Biology
Chemistry
Chemistry, Multidisciplinary
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
ETHYL-OCTANOATE
ACID
TRANSESTERIFICATION
Online AccessGet more information

Cover

More Information
Summary: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.
ISSN:0904-213X
DOI:10.3891/acta.chem.scand.50-0918