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

被引：63

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

页码：975 / 982

页数：8

共 12 条

[1] What affects the configurational stability of chiral organolithium reagents?
Reich, H.J.
Dykstra, R.R.
Angewandte Chemie (International Edition in English), 1993, 32 (10):
[2] ESTIMATION OF THE CONFIGURATIONAL STABILITY OF CHIRAL ORGANOMETALLIC REAGENTS
HOFFMANN, RW
LANZ, J
METTERNICH, R
TARARA, G
HOPPE, D
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11): : 1145 - 1146
[3] CHIRAL ORGANOMETALLIC REAGENTS .3. ON THE CONFIGURATIONAL STABILITY OF ALPHA-BROMOALKYLLITHIUM COMPOUNDS
HOFFMANN, RW
BEWERSDORF, M
CHEMISCHE BERICHTE, 1991, 124 (05) : 1259 - 1264
[4] CHIRAL ORGANOMETALLIC REAGENTS .8. ON THE CONFIGURATIONAL STABILITY OF ALPHA-HETERO-SUBSTITUTED BENZYLLITHIUM COMPOUNDS
HOFFMANN, RW
RUHL, T
HARBACH, J
LIEBIGS ANNALEN DER CHEMIE, 1992, (07): : 725 - 730
[5] CHIRAL ORGANOMETALLIC REAGENTS .7. ON THE CONFIGURATIONAL STABILITY OF ALPHA-METHYLBENZYLLTHIUM
HOFFMANN, RW
RUHL, T
CHEMLA, F
ZAHNEISEN, T
LIEBIGS ANNALEN DER CHEMIE, 1992, (07): : 719 - 724
[6] CONFIGURATIONAL STABILITY OF CHIRAL ORGANOLITHIUM COMPOUNDS ON THE TIME-SCALE OF THEIR ADDITION TO ALDEHYDES
HOFFMANN, RW
JULIUS, M
CHEMLA, F
RUHLAND, T
FRENZEN, G
TETRAHEDRON, 1994, 50 (20) : 6049 - 6060
[7] CHEMISTRY OF OXAZIRIDINES .5. KINETIC RESOLUTION OF SULFOXIDES USING CHIRAL 2-SULFONYLOXAZIRIDINES
DAVIS, FA
BILLMERS, JM
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (16): : 2672 - 2675
[8] A DFT-derived model predicts solvation-dependent configurational stability of organolithium compounds:: A case study of a chiral α-thioallyllithium compound
Brandt, P
Haeffner, F
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) : 48 - 49
[9] ASYMMETRIC INDUCTION BY CHIRAL HETEROCYCLIC-COMPOUNDS - HIGHLY DIASTEREOSELECTIVE REACTION OF 5-OXA-7,8A-DIAZAPERHYDROAZULEN-8-ONES WITH ORGANOMETALLIC REAGENTS
TAKAHASHI, H
MORIMOTO, I
HIGASHIYAMA, K
HETEROCYCLES, 1990, 30 (01) : 287 - 290
[10] CHIRAL ORGANOMETALLIC REAGENTS .16. ENANTIOMERIZATION OF ALPHA-THIO-SUBSTITUTED, ALPHA-SELENO-SUBSTITUTED, AND ALPHA-TELLURO-SUBSTITUTED ALKYLLITHIUM COMPOUNDS - KINETIC AND MECHANISTIC STUDIES
HOFFMANN, RW
DRESS, RK
RUHLAND, T
WENZEL, A
CHEMISCHE BERICHTE, 1995, 128 (09) : 861 - 870

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