Lipase-catalysed resolution of 2-dialkylaminomethylcyclohexanols

被引:30
作者
Forró, E
Kanerva, LT [1 ]
Fülöp, F
机构
[1] Univ Turku, Dept Chem, FIN-20014 Turku, Finland
[2] Univ Turku, Dept Biomed, FIN-20014 Turku, Finland
[3] Albert Szent Gyorgyi Med Univ, Inst Pharmaceut Chem, H-6701 Szeged, Hungary
关键词
D O I
10.1016/S0957-4166(98)00019-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The lipase PS-and Novozym 435-catalysed resolutions of 2-dialkylaminomethylcyclohexanols (A-F) with various vinyl esters were studied in different organic media. High enantioselectivity (E>200) was observed when vinyl acetate was used as an acylating agent and diethyl ether as a solvent. The (1R,2R) enantiomers react preferentially in the case of the cis isomers, whereas the (1R,2S) enantiomers do so in the case of the trans counterparts, Reaction rates were markedly affected by the solvent and by the quantity of the enzyme. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:513 / 520
页数:8
相关论文
共 28 条
[1]   PREPARATION AND PROPERTIES OF 2-(DIALKYLAMINOMETHYL)CYCLOHEXYL AND 2-(DIALKYLAMINOMETHYL)PHENYL CARBANILATES [J].
BRADLEROVA, A ;
PRONAYOVA, N ;
MISIKOVA, E ;
DURINDA, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1990, 55 (07) :1854-1865
[2]   A STRUCTURAL BASIS FOR THE CHIRAL PREFERENCES OF LIPASES [J].
CYGLER, M ;
GROCHULSKI, P ;
KAZLAUSKAS, RJ ;
SCHRAG, JD ;
BOUTHILLIER, F ;
RUBIN, B ;
SERREQI, AN ;
GUPTA, AK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3180-3186
[3]   HIGHLY STEREOSELECTIVE SYNTHESES INVOLVING N-ALKYL-4,4,7-ALPHA-TRIMETHYL-TRANS-OCTAHYDRO-1,3-BENZOXAZINE INTERMEDIATES .2. [J].
ELIEL, EL ;
HE, XC .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2114-2119
[4]   Preparation of the stereoisomers of 2-cyanocycloalkanols by lipase-catalysed acylation [J].
Forro, E ;
Lundell, K ;
Fulop, F ;
Kanerva, LT .
TETRAHEDRON-ASYMMETRY, 1997, 8 (18) :3095-3099
[5]  
Fulop F, 1998, ADV HETEROCYCL CHEM, V69, P349
[6]  
FULOP F, 1991, SYNTHESIS-STUTTGART, P43
[7]  
GREGAN F, 1995, PHARMAZIE, V50, P772
[8]   PREPARATION OF RACEMIC CIS AND TRANS-2-(2-ALKOXYPHENYL-CARBAMOYLOXY)CYCLOHEPTYLMETHYLPIPERIDINIUM CHLORIDES [J].
GREGAN, F ;
KETTMANN, V ;
NOVOMESKY, P ;
SIVY, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1994, 59 (03) :675-682
[9]   A novel chiral super-Lewis acidic catalyst for enantioselective synthesis [J].
Hayashi, Y ;
Rohde, JJ ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (23) :5502-5503
[10]   TEMPERATURE AS AN ENANTIOSELECTIVE PARAMETER IN ENZYMATIC RESOLUTIONS OF RACEMIC MIXTURES [J].
HOLMBERG, E ;
HULT, K .
BIOTECHNOLOGY LETTERS, 1991, 13 (05) :323-326