An enantioselective NMR shift reagent for cationic aromatics

被引：42

作者：

Dignam, CF ^{[1
]}

Richards, CJ ^{[1
]}

Zopf, JJ ^{[1
]}

Wacker, LS ^{[1
]}

Wenzel, TJ ^{[1
]}

机构：

[1] Bates Coll, Dept Chem, Lewiston, ME 04240 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 09期

关键词：

D O I：

10.1021/ol050355t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The water-soluble tetra L-prolinylmethyl derivative of a tetrasulfonated calix[4]resorcarene is an effective chiral NMR solvating agent for compounds with bicyclic aromatic or indole rings. Complexation of bicyclic substrates with the calix[4]resorcarene is likely promoted by hydrophobic effects. The bicyclic substrates have larger association constants with the calix[4]resorcarene than similar phenyl-containing compounds. Substantial enantiomeric discrimination is observed for several resonances in the H-1 NMR spectra of these substrates.

引用

页码：1773 / 1776

页数：4

共 33 条

[1] CALIXARENES .15. THE FORMATION OF COMPLEXES OF CALIXARENES WITH NEUTRAL ORGANIC-MOLECULES IN SOLUTION
BAUER, LJ
GUTSCHE, CD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (21) : 6063 - 6069
[2] CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES
BOHMER, V
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07): : 713 - 745
[3] APPLICATION OF CYCLODEXTRINS TO CHIRAL ANALYSIS BY H-1-NMR SPECTROSCOPY
CASY, AF
MERCER, AD
[J]. MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (09) : 765 - 774
[4] Bioharmaceutical applications of calixarenes
Da Silva, E
Lazar, AN
Coleman, AW
[J]. JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, 2004, 14 (01) : 3 - 20
[5] Determination of association constants (Ka) from solution NMR data
Fielding, L
[J]. TETRAHEDRON, 2000, 56 (34) : 6151 - 6170
[6] FLORINE NUCLEAR MAGNETIC RESONANCE DETERMINATION OF ASSOCIATION CONSTANT OF AN ORGANIC ELECTRON-DONOR-ACCEPTOR COMPLEX
FOSTER, R
FYFE, CA
[J]. CHEMICAL COMMUNICATIONS, 1965, (24) : 642 - &
[7] INTERACTION OF ELECTRON ACCEPTORS WITH BASES .15. DETERMINATION OF ASSOCIATION CONSTANTS OF ORGANIC CHARGE-TRANSFER COMPLEXES BY NMR SPECTROSCOPY
FOSTER, R
FYFE, CA
[J]. TRANSACTIONS OF THE FARADAY SOCIETY, 1965, 61 (512P): : 1626 - &
[8] ON THE USE OF THE METHOD OF CONTINUOUS VARIATIONS
GIL, VMS
OLIVEIRA, NC
[J]. JOURNAL OF CHEMICAL EDUCATION, 1990, 67 (06) : 473 - 478
[9] Chiral resolution of the enantiomers of phenylglycinol using (S)-di-naphthylprolinol calix[4]arene by capillary electrophoresis and fluorescence spectroscopy
Grady, T
Joyce, T
Smyth, MR
Harris, SJ
Diamond, D
[J]. ANALYTICAL COMMUNICATIONS, 1998, 35 (04): : 123 - 125
[10] Healy LO, 1998, ANAL LETT, V31, P1543

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