Synthesis of chiral 18-crown-6 ethers containing lipophilic chains and their enantiomeric recognition of chiral ammonium picrates

被引:62
作者
Colera, M
Costero, AM
Gaviña, P
Gil, S
机构
[1] Univ Valencia, Dept Quim Organ, Valencia 46100, Spain
[2] Univ Valencia, Inst Ciencia Mol, Valencia 46100, Spain
关键词
D O I
10.1016/j.tetasy.2005.06.039
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Four new chiral 18-crown-6 ethers have been prepared to be used in enantiomeric recognition and extraction. The influence of the lipophilic character and bulkiness of the substituents on the complexation of different chiral ammonium picrates in CD3CN has been evaluated. Racemic aqueous solutions of the ammonium salts have been enriched in one enantionter after extraction experiments, and the enantiomeric excesses have been calculated. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2673 / 2679
页数:7
相关论文
共 20 条
[11]   POLYFUNCTIONAL CHIRAL MACROCYCLIC POLYETHER DERIVED FROM L-(+)-TARTARIC ACID [J].
GIRODEAU, JM ;
LEHN, JM ;
SAUVAGE, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (11) :764-764
[12]   FACTORS INFLUENCING ENANTIOMERIC RECOGNITION OF PRIMARY ALKYLAMMONIUM SALTS BY PYRIDINO-18-CROWN-6 TYPE LIGANDS [J].
IZATT, RM ;
WANG, TM ;
HATHAWAY, JK ;
ZHANG, XX ;
CURTIS, JC ;
BRADSHAW, JS ;
ZHU, CY .
JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1994, 17 (02) :157-175
[13]   SYNTHETIC CHIRAL MACROCYCLIC CROWN LIGANDS - A SHORT REVIEW [J].
JOLLEY, ST ;
BRADSHAW, JS ;
IZATT, RM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (01) :3-19
[14]  
KHOLIN YV, 1999, KHARKOV U B 26, V437, P17
[15]  
Mash E. A., 1993, ORG SYNTH, V8, P155
[16]  
MASH EA, 1989, ORG SYNTH, V68, P92
[17]  
Miethchen R, 1998, SYNTHESIS-STUTTGART, P94
[18]   HOST-GUEST COMPLEXATION .4. REMOTE SUBSTITUENT EFFECTS ON MACROCYCLIC POLYETHER BINDING TO METAL AND AMMONIUM-IONS [J].
MOORE, SS ;
TARNOWSKI, TL ;
NEWCOMB, M ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (19) :6398-6405
[19]   CHIRAL CROWN ETHERS [J].
STODDART, JF .
TOPICS IN STEREOCHEMISTRY, 1987, 17 :207-288
[20]   Enantiomeric recognition of amine compounds by chiral macrocyclic receptors [J].
Zhang, XX ;
Bradshaw, JS ;
Izatt, RM .
CHEMICAL REVIEWS, 1997, 97 (08) :3313-3361