Enantiomeric excess determination of some chiral sulfoxides by NMR: Use of (S)-Ibuprofenρ and (S)-Naproxenρ as shift reagents

Tetrahedron Letters

Volumn 38, Issue 45, 1997, Pages 7875-7878

  Fauconnot, Laëtitia ^a   Nugier Chauvin, Caroline ^a   Noiret, Nicolas ^a   Patin, Henri ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IBUPROFEN; NAPROXEN; SULFOXIDE;

ANISOTROPY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030728759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10153-8     Document Type: Article

References (16)

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2. (b) Deshmukh, M.; Dunach, E.; Juge, S.; Kagan, H.B. Tetrahedron Lett. 1984, 25, 3467-3470.
3. (c) Drabowicz, J.; Duddek, H. Sulfur Lett. 1989, 10, 37-40.
4. (d) Drabowicz, J.; Dudzinski, B.; Mikolajczyk, M..Tetrahedron : Asymmetry 1992, 3, 1231-1234.
5. (a) Buist, P.H.; Marecak, D.M. J. Am. Chem. Soc. 1992, 114, 5073-5080.
6. (b) Tetrahedron: Asymmetry 1995, 6, 7-10.
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11. Gautier, N.; Noiret, N.; Nugier-Chauvin, C.; Patin, H. Tetrahedron: Asymmetry 1997, 8, 501-505.
12. Latypov, Sh. K.; Seco, J.M.; Quiñoa, E.; Riguera, R. J. Org. Chem. 1995, 60, 504-515.
13. See for example; (a) Bruna, K.; Geisslinger, G.; Menzel-Soglowok, S. J. Clin. Pharmacol. 1992, 32, 944.
14. (c) Wechter, W.J.; Bigornie, A.E.; Murray, E.D., Jr.; Levine, B.H.; Young, J.W. Chirality 1993, 5, 492-494.
15. Comparative commercial prices for 1g of shift reagent : (S)-MPA/(S)-Naproxen ∼ 465/33.
16. NMR spectra were recorded with a ARX 400 Bruker spectrometer. The correct assignements were established using routine COSY and HMQC experiments. All the samples were prepared as follows : to 1 mg of the sulfoxide in 0.5 mL of solvent was added 3 molar eq. of the desired NMR shift reagent. All the spectra were recorded at 298K.