ENANTIOSELECTIVE EPOXIDATION BY AN OPTICALLY-ACTIVE HYDROPEROXIDE

被引:24
作者
HAMANN, HJ [1 ]
HOFT, E [1 ]
CHMIELEWSKI, M [1 ]
MACIEJEWSKI, S [1 ]
机构
[1] POLISH ACAD SCI,INST ORGAN CHEM,WARSAW 42,POLAND
关键词
ASYMMETRIC INDUCTION; CAPILLARY GAS CHROMATOGRAPHY; CYCLODEXTRIN STATIONARY PHASES;
D O I
10.1002/chir.530050511
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Enantioselective epoxidation of prochiral allylic alcohols with optically active 4,6-di-O-acetyl-2,3-dideoxy-alpha-D-threo-hex-2-enopyranosyl hydroperoxide in the presence of Ti(O-i-Pr)4 gives chiral epoxy alcohols with moderate enantiomeric excess. (C) 1993 Wiley-Liss, Inc.
引用
收藏
页码:338 / 340
页数:3
相关论文
共 16 条
[1]   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
[2]   STABLE, ENANTIOMERICALLY PURE HYDROPEROXIDES DERIVED FROM SUGARS [J].
CHMIELEWSKI, M ;
JURCZAK, J ;
MACIEJEWSKI, S .
CARBOHYDRATE RESEARCH, 1987, 165 (01) :111-115
[3]   A NEW SYNTHON FOR OPTICALLY-ACTIVE DIENE HYDROPEROXIDES [J].
DUSSAULT, P ;
LEE, IQ ;
KREIFELS, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4087-4089
[4]   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
[5]   2-METHOXYPROP-2-YL HYDROPEROXIDE - A CONVENIENT REAGENT FOR THE SYNTHESIS OF HYDROPEROXIDES AND PERACIDS [J].
DUSSAULT, P ;
SAHLI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1009-1012
[6]  
Finn M. G., 1985, ASYMMETRIC SYNTHESIS, V5, P247
[7]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[8]  
HOFT E, 1991, DIOXYGEN ACTIVATION, P537
[9]   PREPARATIVE, ENZYMATIC-SYNTHESIS OF LINOLEIC-ACID (13S)-HYDROPEROXIDE USING SOYBEAN LIPOXYGENASE-1 [J].
IACAZIO, G ;
LANGRAND, G ;
BARATTI, J ;
BUONO, G ;
TRIANTAPHYLIDES, C .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1690-1691
[10]  
KONIG WA, 1990, KONTAKTE DARMSTADT, V2, P3