Analysis of the 13C NMR spectra of molecules, chiral by isotopic substitution, dissolved in a chiral oriented environment: Towards the absolute assignment of the pro-R/pro-S character of enantiotopic ligands in prochiral molecules

Chemistry - A European Journal

Volumn 10, Issue 15, 2004, Pages 3741-3746

  Lesot, Philippe ^a   Lafon, Olivier ^a   Courtieu, Jacques ^a   Berdagué, Philippe ^a  

^a CNRS   (France)

Author keywords

Chirality; Enantioselectivity; Isotope effect; Liquid crystals; NMR spectroscopy

Indexed keywords

ANISOTROPY; DEUTERIUM; ISOTOPES; METHANOL; MOLECULAR ORIENTATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; SUBSTITUTION REACTIONS;

ISOTOPE EFFECTS; ISOTOPIC SUBSTITUTION;

NEMATIC LIQUID CRYSTALS;

ANISOTROPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DISSOLUTION; ENANTIOMER; ENANTIOSELECTIVITY; LIQUID CRYSTAL; MOLECULAR MECHANICS; PROTON TRANSPORT; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 4243190114     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400065     Document Type: Article

References (25)

1. M. Sarfati, P. Lesot, D. Merlet, J. Courtieu, Chem. Commun. 2000, 2069-2081, and references therein.
2. P. Lesot, M. Sarfati, J. Courtieu, Chem. Eur. J. 2003, 9, 1724-1745.
3. C. Aroulanda, M. Sarfati, J. Courtieu, P. Lesot, Enantiomer 2001, 6, 281-287.
4. a) P. Lesot, D. Merlet, T. P. Rantala, J. Jokisaari, J. W. Emsley, J. Courtieu, J. Phys. Chem. A 1997, 101, 5719-5724;
5. b) J. W. Emsley, P. Lesot, D. Merlet, Phys. Chem. Chem. Phys. 2004, 6, 522-530.
6. A. Meddour, I. Canet, A. Loewenstein, J. M. Péchiné, J. Courtieu, J. Am. Chem. Soc. 1995, 116, 9652-9656.
7. a) D. Merlet, A. Loewenstein, W. Smadja, J. Courtieu, P. Lesot, J. Am. Chem. Soc. 1998, 120, 963-969;
8. b) D. Merlet, J. W. Emsley, P. Lesot, J. Courtieu, J. Chem. Phys. 1999, 111, 6890-6896.
9. P. Lesot, D. Merlet, M. Sarfati, J. Courtieu, H. Zimmermann, Z. Luz, J. Am. Chem. Soc. 2002, 124, 10071-10082.
10. C. Aroulanda, D. Merlet, J. Courtieu, P. Lesot, J. Am. Chem. Soc. 2001, 123, 12059-12066.
11. P. Lesot, D. Merlet, A. Meddour, A. Loewenstein, J. Courtieu, J. Chem. Soc. Faraday Trans. 1995, 91, 1371-1375.
12. A. Meddour, P. Berdagué, A. Hedli, J. Courtieu, P. Lesot, J. Am. Chem. Soc. 1997, 119, 4502-4508.
13. a) P. E. Hansen, Ann. Rep. NMR Spectrosc. 1983, 15, 105-231;
14. b) P. E. Hansen, Prog. Nucl. Magn. Reson. Spectrosc. 1988, 20, 207-257;
15. c) J. R. Wesener, D. Moskau, H. Günther, Tetrahedron. Lett. 1985, 26, 1491-1492;
16. d) S. Berger, Isotope Effects in NMR Spectroscopy, NMR Basic Principles and Progress, Vol. 2, Springer, 1990, p. 1;
17. e) C. J. Jameson, in Encyclopedia of NMR (Eds.: G. M. Grant, R. K. Harris), Wiley, Chichester, 1995, pp. 2638-2655.
18. H. A. Kalinowski, S. Berger, S. Braun, in Carbon-13 NMR Spectroscopy, Wiley, New York, 1988.
19. P. L. Rinaldi, N. J. Baldwin, J. Am. Chem. Soc. 1982, 104, 5791-5793.
20. a) R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-433; Angew. Chem. Int. Ed. Engl. 1966, 5, 385-415;
21. a) R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-433; Angew. Chem. Int. Ed. Engl. 1966, 5, 385-415;
22. b) A. L. Eliel, A. H. Wilen, in Stereochemistry of Organic Compounds, Wiley, New York, 1594.
23. C. Canlet, D. Merlet, P. Lesot, A. Meddour, A. Loewenstein, J. Courtieu, Tetrahedron: Asymmetry 2000, 11, 1911-1918.
24. R. H. Newman-Evans, R. J. Simon, B. K. Carpenter, J. Org. Chem. 1990, 55, 695-711.
25. G. R. Sood, D. M. Ashworth, A. A. Ajaz, J. A. Robinson, J. Chem. Soc. Perkin Trans. 1988, 1, 3183-3193.