Enantiomeric perturbation of equilibria. Differential solvation of a chiral lithium amide by the enantiomers of 2-methyltetrahydrofuran measured by NMR spectroscopy

Journal of the American Chemical Society

Volumn 118, Issue 14, 1996, Pages 3539-3540

  Hilmersson, Göran ^a   Ahlberg, Per ^a   Davidsson, Öjvind ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOLITHIUM COMPOUND;

ARTICLE; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE;

EID: 0029959901     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9540740     Document Type: Article

References (14)

1. (a) Lucht, B. L , Collum, D. B. J. Am. Chem. Soc. 1994, 116, 6009.
2. (b) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 9863.
3. Slow ligand exchange rates have also been reported with HMPA and diamines, see: (a) Reich, H. J.; Green, D. P. J. Am. Chem. Soc. 1989, 111, 8729. (b) Barr, D.; Doyle, M. J.; Mulvey, R. E.; Raithby, P. R , Reed, D.; Snaith, R.; Wright, D. S. J. Chem. Soc., Chem. Commun. 1989, 318. (c) Fraenkel, G.; Chow, A., Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 1282. Boche, G.; Fraenkel, G.; Cabral, J.; Harms, K.; van Eikema Hommes, N. J. R.; Lohrenz, J.; Marsch, M.; Schleyer, P.v.R. J. Am. Chem. Soc. 1992, 114, 1562. (e) Hoffman, R. W.; Klute, W.; Dress, R. K.; Wenzel, A. J. Chem. Soc., Perkin Trans. 2 1995, 1721.
4. Slow ligand exchange rates have also been reported with HMPA and diamines, see: (a) Reich, H. J.; Green, D. P. J. Am. Chem. Soc. 1989, 111, 8729. (b) Barr, D.; Doyle, M. J.; Mulvey, R. E.; Raithby, P. R , Reed, D.; Snaith, R.; Wright, D. S. J. Chem. Soc., Chem. Commun. 1989, 318. (c) Fraenkel, G.; Chow, A., Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 1282. Boche, G.; Fraenkel, G.; Cabral, J.; Harms, K.; van Eikema Hommes, N. J. R.; Lohrenz, J.; Marsch, M.; Schleyer, P.v.R. J. Am. Chem. Soc. 1992, 114, 1562. (e) Hoffman, R. W.; Klute, W.; Dress, R. K.; Wenzel, A. J. Chem. Soc., Perkin Trans. 2 1995, 1721.
5. Slow ligand exchange rates have also been reported with HMPA and diamines, see: (a) Reich, H. J.; Green, D. P. J. Am. Chem. Soc. 1989, 111, 8729. (b) Barr, D.; Doyle, M. J.; Mulvey, R. E.; Raithby, P. R , Reed, D.; Snaith, R.; Wright, D. S. J. Chem. Soc., Chem. Commun. 1989, 318. (c) Fraenkel, G.; Chow, A., Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 1282. Boche, G.; Fraenkel, G.; Cabral, J.; Harms, K.; van Eikema Hommes, N. J. R.; Lohrenz, J.; Marsch, M.; Schleyer, P.v.R. J. Am. Chem. Soc. 1992, 114, 1562. (e) Hoffman, R. W.; Klute, W.; Dress, R. K.; Wenzel, A. J. Chem. Soc., Perkin Trans. 2 1995, 1721.
6. Slow ligand exchange rates have also been reported with HMPA and diamines, see: (a) Reich, H. J.; Green, D. P. J. Am. Chem. Soc. 1989, 111, 8729. (b) Barr, D.; Doyle, M. J.; Mulvey, R. E.; Raithby, P. R , Reed, D.; Snaith, R.; Wright, D. S. J. Chem. Soc., Chem. Commun. 1989, 318. (c) Fraenkel, G.; Chow, A., Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 1282. Boche, G.; Fraenkel, G.; Cabral, J.; Harms, K.; van Eikema Hommes, N. J. R.; Lohrenz, J.; Marsch, M.; Schleyer, P.v.R. J. Am. Chem. Soc. 1992, 114, 1562. (e) Hoffman, R. W.; Klute, W.; Dress, R. K.; Wenzel, A. J. Chem. Soc., Perkin Trans. 2 1995, 1721.
7. Slow ligand exchange rates have also been reported with HMPA and diamines, see: (a) Reich, H. J.; Green, D. P. J. Am. Chem. Soc. 1989, 111, 8729. (b) Barr, D.; Doyle, M. J.; Mulvey, R. E.; Raithby, P. R , Reed, D.; Snaith, R.; Wright, D. S. J. Chem. Soc., Chem. Commun. 1989, 318. (c) Fraenkel, G.; Chow, A., Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 1282. Boche, G.; Fraenkel, G.; Cabral, J.; Harms, K.; van Eikema Hommes, N. J. R.; Lohrenz, J.; Marsch, M.; Schleyer, P.v.R. J. Am. Chem. Soc. 1992, 114, 1562. (e) Hoffman, R. W.; Klute, W.; Dress, R. K.; Wenzel, A. J. Chem. Soc., Perkin Trans. 2 1995, 1721.
8. Hilmersson, G.; Davidsson, Ö. J. Organomet. Chem. 1995, 489, 175.; J. Org. Chem. 1995, 60, 7660.
9. Hilmersson, G.; Davidsson, Ö. J. Organomet. Chem. 1995, 489, 175.; J. Org. Chem. 1995, 60, 7660.
10. 2 has been determined by X-ray crystallography, Hilmersson, G.; Davidsson, Ö: Håkansson, M. Manuscript in preparation.
11. 13C NMR spectral width was 25 000 Hz, and 2000 transients were collected with 128 000 data points for each spectra. Zero-filling to 512 000 data points gave a digital resolution of less than 0.1 Hz. The probe temperature was calibrated (±0.5°C) with a standard methanol thermometer after more than 1 h of temperature equilibration.
12. Parker, D. Chem. Rev. 1991, 91, 1441 and references cited therein.
13. Saunders, M.; Vogel, P.; Jaffe, M. H. J. Am. Chem. Soc. 1971, 93, 2558.
14. Isotope effects on NMR spectra of equilibrating systems have been reviewed by Siehl. H.-U. Adv. Phys. Org. Chem. 1987, 23, 463.