Chemoenzymatic preparation of optically active β-amino-cyclohexanols and their application in the enantioselective addition of diethylzinc to benzaldehyde

被引:17
作者
González-Sabín, J [1 ]
Gotor, V [1 ]
Rebolledo, F [1 ]
机构
[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain
关键词
D O I
10.1016/j.tetasy.2004.03.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Optically active vesamicol and other trans-2-(N,N-dialkylamino)cyclohexanols have been easily prepared in a two step sequence: opening of the oxirane ring of cyclohexene oxide with a secondary amine and subsequent resolution of the resulting racemic amino alcohol by transesterification catalyzed by Pseudomonas ccpacia lipase. The utility of these beta-aminocyclohexanols as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde has also been investigated. (C) 2004 Elsevier Ltd. All rights reserved.
引用
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页码:1335 / 1341
页数:7
相关论文
共 33 条
[1]  
ABICO A, 1992, TETRAHEDRON LETT, V33, P5517
[2]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[3]  
BAIN AI, 1999, Patent No. 9950225
[4]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[5]   Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol:: a combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution [J].
Clariana, J ;
García-Granda, S ;
Gotor, V ;
Gutiérrez-Fernández, A ;
Luna, A ;
Moreno-Mañas, M ;
Vallribera, A .
TETRAHEDRON-ASYMMETRY, 2000, 11 (22) :4549-4557
[6]  
Coppola G.M., 1987, ASYMMETRIC SYNTHESIS
[7]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[8]   VESAMICOL ANALOGS AS SIGMA-LIGANDS - MOLECULAR DETERMINANTS OF SELECTIVITY AT THE VESAMICOL RECEPTOR [J].
EFANGE, SMN ;
MACH, RH ;
SMITH, CR ;
KHARE, AB ;
FOULON, C ;
AKELLA, SK ;
CHILDERS, SR ;
PARSONS, SM .
BIOCHEMICAL PHARMACOLOGY, 1995, 49 (06) :791-797
[9]   BORANES IN SYNTHESIS .5. THE HYDROBORATION OF ENAMINES WITH MONOALKYLBORANES AND DIALKYLBORANES - ASYMMETRIC-SYNTHESIS OF BETA-AMINO ALCOHOLS OF MODERATE ENANTIOMERIC PURITY FROM ALDEHYDE ENAMINES [J].
FISHER, GB ;
GORALSKI, CT ;
NICHOLSON, LW ;
HASHA, DL ;
ZAKETT, D ;
SINGARAM, B .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2026-2034
[10]  
Garcia-Alles LF, 1998, BIOTECHNOL BIOENG, V59, P684, DOI 10.1002/(SICI)1097-0290(19980920)59:6<684::AID-BIT5>3.0.CO