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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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