Choosing the Right Reagent for the Determination of the Absolute Configuration of Amines by NMR: MTPA or MPA?

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7569-7574

  Seco, J M ^a   Latypov, Sh K ^a,b   Quinoa E ^a   Riguera, R ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000953504     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970427x     Document Type: Article

References (16)

1. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.
2. (b) Trost, B. M.; Belletire, J. L.; Goldleski, P. G.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374.
3. (c) For a review see: Uray, G. In Houben-Weyl Methods in Organic Chemistry; (Helchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E.; Eds.; Thieme: Stuttgart, 1996, Vol. 1, p 253. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994.
4. (c) For a review see: Uray, G. In Houben-Weyl Methods in Organic Chemistry; (Helchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E.; Eds.; Thieme: Stuttgart, 1996, Vol. 1, p 253. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994.
5. RS is the difference in the chemical shifts between (R)-MTPA (or (R)-MPA) and (S)-MTPA (or (S)-MPA) derivatives.
6. (a) Latypov, Sh. K.; Seco, J. M.; Quíñoá, E.; Riguera, R. J. Org. Chem. 1995, 60, 504-515.
7. (b) Seco, J. M.; Latypov, Sh. K.; Quiñoá, E.; Riguera, R. Tetrahedron Lett. 1994, 35, 2921-2924.
8. (c) Seco, J. M.; Latypov, Sh. K.; Quiñoá, E.; Riguera, R. Tetrahedron Asymmetry 1995, 6, 107-110.
9. (d) Latypov, Sh. K.; Seco, J. M.; Quiñoà, E.; Riguera, R. J. Org. Chem. 1995, 60, 1538-1545.
10. (e) Latypov, Sh. K.; Seco, J. M.; Quiñoá, Riguera, R. J. Org. Chem. 1996, 61, 8569-8577.
11. Haigh, C. W.; Mallion, R. B. Progress in NMR Spectroscopy; Pergamon Press, Ltd.: New York, 1980; Vol. 13, pp 303-344.
12. (a) For simplification purposes and in coherence with previous papers (see ref 3), we will refer to these compounds by (R/S)-n, where (R/S) indicates the configuration at the chiral center of the auxiliary reagent (MPA or MTPA) and n is the digit that identifies the parent alcohol or amine.
13. (b) For data on compounds 8, 10, 12, and 14, see reference 3d; for compounds 7, 9, 11, 13, 15-20, see: Kusumi, T.; Fukushima, T.; Ohtani, I.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939-2942; for compound 21 see reference 3e.
14. 2 4/1, T = 183 K): δ(10′) = 0.817 ppm.
15. (a) Lee, M.; Lown, J. W. J. Org. Chem. 1987, 52, 5717-5721.
16. (b) Mikolajczyk, M.; Kielbasinski, P. Tetrahedron 1981, 37, 233-284.