Acetyl-d3 chloride: A convenient nonchiral derivatizing agent (NCDA) for a facile enantiomeric excess determination of amines through deuterium NMR

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 9035-9037

  Canet, Jean Louis ^a,c   Canet, Isabelle ^a   Courtieu, Jacques ^b   Da Suva, Sandrine ^a   Gelas, Jacques ^b   Troin, Yves ^a  

^a Ecole Nationale Superieure de Chimie de Clermont Ferrand   (France)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010882677     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961141f     Document Type: Article

References (10)

1. For reviews, see: (a) Parker, D. Chem. Rev. 1991, 91, 1441.
2. (b) Hulst, R; Kellog, R. M.; Feringa, B. L. Réel. Trau. Chlm. Pays-Bas 1995, 114, 115.
3. Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326 and references cited therein.
4. (a) Canet, I.; Courtieu, J.; Lwenstein, A.; Meddour, A.; Pechine, J. M. J. Am. Chem. Soc. 1995, 117, 6520.
5. (b) Meddour, A.; Canet, I.; Lœwenstein, A.; Pechine, J. M.; Courtieu, J. J. Am. Chem. Soc. 1994, 776, 9652.
6. Canet, I.; Meddour, A.; Courtieu, J.; Canet, J. L.; Salaiin, J. J. Am. Chem. Soc. 1994, 776, 2155.
7. Borch, R. F.; Bernstein, M. D.; Dupont Durst, H. J. Am. Chem. Soc. 1971, 93, 2897.
8. Using 5 mm tubes in a 10 mm probe leads to 5 Hz line widths. Better resolution (1-3 Hz) is obtained using a selective 5 mm deuterium probe (see ref 3).
9. (R)-(+)-α-MethylbenzyIamine (96 ee) and (S)-(-)-α-methylbenzylamine (99 ee) were purchased from Acros.
10. When two doublets are obtained, the difference between the visualization of enantiomers (doublets are centered on the same frequency and have the same intensities) and a coalescence phenomenon (doublets are not centered or intensities are different) can be determined easily.