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

被引:19
作者
Mattson, A
Orrenius, C
Ohrner, N
Unelius, CR
Hult, K
Norin, T
机构
[1] ROYAL INST TECHNOL,DEPT CHEM ORGAN CHEM,S-10044 STOCKHOLM,SWEDEN
[2] ROYAL INST TECHNOL,DEPT BIOCHEM & BIOTECHNOL,S-10044 STOCKHOLM,SWEDEN
来源
ACTA CHEMICA SCANDINAVICA | 1996年 / 50卷 / 10期
关键词
D O I
10.3891/acta.chem.scand.50-0918
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
引用
收藏
页码:918 / 921
页数:4
相关论文
共 14 条
[1]   CLAISEN REARRANGEMENTS WITH MESITYL OXIDE DIMETHYL KETAL - SYNTHESIS OF IPSDIENONE, E-OCIMENONE, AND Z-OCIMENONE, 2,6-DIMETHYL-2,7-OCTADIEN-4-ONE AND 2,6-DIMETHYL-2,7-OCTADIEN-4-OL [J].
BAECKSTROM, P ;
STRIDH, K ;
LI, L ;
NORIN, T .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1987, 41 (06) :442-447
[2]   STEREOSELECTIVITY IN THE EPOXIDE HYDRASE CATALYZED-HYDROLYSIS OF THE STEREOISOMERIC 4-TERT-BUTYL-1,2-EPOXYCYCLOHEXANES [J].
BELLUCCI, G ;
BERTI, G ;
INGROSSO, G ;
MASTRORILLI, E .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (02) :299-303
[3]   SYNTHESIS OF 2,5-DIISOXAZOLYLTETRAHYDROFURANS [J].
CHIARINO, D ;
FANTUCCI, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (07) :1705-1708
[4]   PREPARATION AND REACTIONS OF DIALKOXYTETRAHYDROFURANS [J].
FAKSTORP, J ;
RALEIGH, D ;
SCHNIEPP, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (02) :869-875
[5]   S-ETHYL THIOOCTANOATE AS ACYL DONOR IN LIPASE CATALYZED RESOLUTION OF SECONDARY ALCOHOLS [J].
FRYKMAN, H ;
OHRNER, N ;
NORIN, T ;
HULT, K .
TETRAHEDRON LETTERS, 1993, 34 (08) :1367-1370
[7]   RESOLUTION OF DIOLS WITH C2-SYMMETRY BY LIPASE-CATALYZED TRANSESTERIFICATION [J].
MATTSON, A ;
OHRNER, N ;
HULT, K ;
NORIN, T .
TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :925-930
[8]   DISPLACEMENT OF THE EQUILIBRIUM IN LIPASE CATALYZED TRANSESTERIFICATION IN ETHYL OCTANOATE BY CONTINOUS EVAPORATION OF ETHANOL [J].
OHRNER, N ;
MARTINELLE, M ;
MATTSON, A ;
NORIN, T ;
HULT, K .
BIOTECHNOLOGY LETTERS, 1992, 14 (04) :263-268
[9]   THIOETHYL-OCTANOATE, VINYL-OCTANOATE, ETHYL-OCTANOATE ESTERS AND OCTANOIC-ACID AS ACYL DONORS IN LIPASE-CATALYZED ACYL TRANSFER-REACTIONS [J].
OHRNER, N ;
MARTINELLE, M ;
MATTSON, A ;
NORIN, T ;
HULT, K .
BIOCATALYSIS, 1994, 9 (1-4) :105-114
[10]  
SKATTEBOL L, 1963, ORG SYNTH, V4, P792