CHIRAL ORGANOMETALLIC REAGENTS .5. A TEST ON THE CONFIGURATIONAL STABILITY OF CHIRAL ORGANOLITHIUM COMPOUNDS BASED ON KINETIC RESOLUTION - SCOPE AND LIMITATIONS

被引:64
作者
HIRSCH, R [1 ]
HOFFMANN, RW [1 ]
机构
[1] UNIV MARBURG,FACHBEREICH CHEM,HANS MEERWEIN STR,W-3550 MARBURG,GERMANY
来源
CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 04期
关键词
CONFIGURATIONAL STABILITY; KINETIC RESOLUTION;
D O I
10.1002/cber.19921250432
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The test on the configurational stability of chiral organolithium compounds is based on the kinetic resolution of the racemic organolithium compound on reaction with an enantiomerically pure electrophile. The limits of this test have been evaluated by model calculations. The factors that have been considered are: Optimum values for the kinetic resolution; effects of < 100% enantiomeric purity of the chiral electrophile; parallel side reactions of the organolithium compounds with the electrophile.
引用
收藏
页码:975 / 982
页数:8
相关论文
共 42 条
[1]   D-GLYCOPYRANOSYL PHENYLSULFONES - THEIR USE IN A STEREOCONTROL SYNTHESIS OF CIS-2,6-DISUBSTITUTED TETRAHYDROPYRANS (BETA-D-C-GLYCOSIDES) [J].
BEAU, JM ;
SINAY, P .
TETRAHEDRON LETTERS, 1985, 26 (50) :6189-6192
[2]   PREPARATION AND REDUCTIVE LITHIATION OF 2-DEOXY-D-GLUCOPYRANOSYL PHENYLSULFONES - A HIGHLY STEREOSELECTIVE ROUTE TO C-GLYCOSIDES [J].
BEAU, JM ;
SINAY, P .
TETRAHEDRON LETTERS, 1985, 26 (50) :6185-6188
[3]   UNLIMITED NONLINEAR SELECTIVITY EFFECTS IN SYSTEMS OF INDEPENDENT PARALLEL REACTIONS AS A BASIS FOR NEW CHEMICAL SEPARATION TECHNIQUES [J].
BRANDT, J ;
JOCHUM, C ;
UGI, I .
TETRAHEDRON, 1977, 33 (11) :1353-1363
[4]   PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-HYDROXY ACID-DERIVATIVES FROM ALPHA-ALKOXYORGANOSTANNANES [J].
CHAN, PCM ;
CHONG, JM .
TETRAHEDRON LETTERS, 1990, 31 (14) :1985-1988
[5]   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
[6]  
CHONG JM, 1990, TETRAHEDRON LETT, V31, P1981
[8]   OPTICALLY-ACTIVE ALLYLSILANES .10. ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .3. PREPARATION OF OPTICALLY-ACTIVE ALLYLSILANES BY PALLADIUM-CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING [J].
HAYASHI, T ;
KONISHI, M ;
OKAMOTO, Y ;
KABETA, K ;
KUMADA, M .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) :3772-3781
[9]  
HIRSCH R, 1992, THESIS U MARBURG
[10]  
HOFFMANN RW, 1988, LIEBIGS ANN CHEM, P161