Preparative scale enantioseparation of 1-cyclohexyl-1-phenylethyl hydroperoxide and 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide on a modified cellulose stationary phase

被引:6
作者
Wagner, J [1 ]
Hamann, HJ [1 ]
Dopke, W [1 ]
Kunath, A [1 ]
Hoft, E [1 ]
机构
[1] INST APPL CHEM ADLERSHOF,BERLIN,GERMANY
关键词
chiral HPLC; cellulose tris(3,5-dimethylphenyl carbamate); hydroperoxides; enantiomers; circular dichroism;
D O I
10.1002/chir.530070410
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The analytical and preparative scale optical resolution of 1-cyclohexyl-1-phenylethyl hydroperoxide and 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide has been achieved by chiral HPLC on a cellulose tris(3,5-dimethylphenyl carbamate) stationary phase coated on silica gel. The method has been used to obtain several hundred milligrams of highly enriched enantiomers (%ee >98) which were characterized by [alpha](D) and circular dichroism spectra, respectively. Configurational assignments were achieved for 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide enantiomers. (C) 1995 Wiley-Liss, Inc.
引用
收藏
页码:243 / 247
页数:5
相关论文
共 18 条
[1]  
Adam W., 1993, ANGEW CHEM, V105, P1800
[2]   ENZYMATIC RESOLUTION OF RACEMIC HYDROPEROXIDES IN ORGANIC-SOLVENT [J].
BABA, N ;
MIMURA, M ;
HIRATAKE, J ;
UCHIDA, K ;
ODA, J .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1988, 52 (10) :2685-2687
[3]   STABLE, ENANTIOMERICALLY PURE HYDROPEROXIDES DERIVED FROM SUGARS [J].
CHMIELEWSKI, M ;
JURCZAK, J ;
MACIEJEWSKI, S .
CARBOHYDRATE RESEARCH, 1987, 165 (01) :111-115
[4]   PREPARATIVE CHROMATOGRAPHIC RESOLUTION OF RACEMATES ON CHIRAL STATIONARY PHASES ON LABORATORY AND PRODUCTION SCALES BY CLOSED-LOOP RECYCLING CHROMATOGRAPHY [J].
DINGENEN, J ;
KINKEL, JN .
JOURNAL OF CHROMATOGRAPHY A, 1994, 666 (1-2) :627-650
[5]   A NEW SYNTHON FOR OPTICALLY-ACTIVE DIENE HYDROPEROXIDES [J].
DUSSAULT, P ;
LEE, IQ ;
KREIFELS, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4087-4089
[6]   THE RESOLUTION OF RACEMIC HYDROPEROXIDES - THE PREPARATION OF OPTICALLY PURE HYDROPEROXIDE NATURAL-PRODUCTS [J].
DUSSAULT, P ;
PORTER, NA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (18) :6276-6277
[7]   BENZOYL CELLULOSE BEADS IN THE PURE POLYMERIC FORM AS A NEW POWERFUL SORBENT FOR THE CHROMATOGRAPHIC RESOLUTION OF RACEMATES [J].
FRANCOTTE, E ;
WOLF, RM .
CHIRALITY, 1991, 3 (01) :43-55
[8]   CHLOROPEROXIDASE-CATALYZED ASYMMETRIC-SYNTHESIS - ENANTIOSELECTIVE REACTIONS OF CHIRAL HYDROPEROXIDES WITH SULFIDES AND BROMOHYDRATION OF GLYCALS [J].
FU, H ;
KONDO, H ;
ICHIKAWA, Y ;
LOOK, GC ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7265-7270
[9]   Autoxidation of hydrocarbons - A tetra-hydro-naphthaline-peroxide received through autoxidation (I Announcement) [J].
Hock, H ;
Susemihl, W .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1933, 66 :61-68
[10]   KINETIC RESOLUTION OF 1-METHYL-1-PHENYLPROPYL HYDROPEROXIDE VIA SHARPLESS EPOXIDATION [J].
HOFT, E ;
HAMANN, HJ ;
KUNATH, A ;
RUFFER, L .
TETRAHEDRON-ASYMMETRY, 1992, 3 (04) :507-510