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1H NMR Spectral Simplification with Chiral Solvating Agents and with Achiral and Chiral...
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1H NMR Spectral Simplification with Chiral Solvating Agents and with Achiral and Chiral Lanthanide Shift Reagents.Cis-4,5-Dihydro-4-Methyl-5-Phenyl-2-Oxazolamine, “Cis-4-Methylaminorex,” a Potent Stimulant and Anorectic
作者:
GaryW. Caldwell,
Robert Rothchild,
Iraida Valentin,
期刊:
Spectroscopy Letters
(Taylor Available online 1990)
卷期:
Volume 23,
issue 5
页码: 589-610
ISSN:0038-7010
年代: 1990
DOI:10.1080/00387019008054442
出版商: Taylor & Francis Group
关键词: 2-Amino-4-methyl-5-phenyl-2-oxazoline;Eu(FOD)3;Eu(HFC)3;Europium;(R)-(-)-2,2,2-Trifluoro-1-(9-anthryl)ethanol;(R)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetic acid;Enantiomer;Optical Purity;Analysis;Stereoisomer
数据来源: Taylor
摘要:
The 60 MHz1H NMR spectra of racemic (+)-cis-4,5-dihydro-4-methyl-5-phenyl-2-oxazolamine,1, have been studied at 28° in CDC13, solution with the achiral lanthanide shift reagent (LSR), tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato) europium(III), 2, and the chiral reagent tris[3−(heptafluoropropylhydroxymethy1ene)-d-camphor-ato]europium(III), 3. Additional NMR studies were performed at 400 MHz in CDC1, solution at 24° using the chiral solvating agents (CSA), (E)-(-)-2,2,2-trifluoro-1- (9-anthryl) ethanol,4, and (R) - (+) -α-methoxy- α-(trifluoromethy1)phenylacetic acid,5. Substantial enantiomeric shift differences, for the CH3, signal of1using3or5, and for the ortho aryl protons using4, which should make possible direct optical purity determinations of1. Accurate 400 MHz data f o r chemical shifts and vicinal coupling constants of, of racemiccis-1are presented, and compared with values for (optically active) (-)-trans-1; some dfferences are seen compared to previously reported data. solution. The LSR and CSA results are compared and Some additional data were obtained in C6D6discussed.
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