Univocal syntheses of 2- and 3-hydroxymethyl-2,3-dihydro[1,4]dioxino[2,3-b] pyridine enantiomers

Tetrahedron Asymmetry

Volumn 16, Issue 20, 2005, Pages 3380-3384

  Bolchi, Cristiano ^a   Pallavicini, Marco ^a   Fumagalli, Laura ^a   Moroni, Barbara ^a   Rusconi, Chiara ^a   Valoti, Ermanno ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYMETHYL 2,3 DIHYDRO[1,4]DIOXINO[2,3 B]PYRIDINE; 3 HYDROXYMETHYL 2,3 DIHYDRO[1,4]DIOXINO[2,3 B]PYRIDINE; GLYCEROL DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL COMPOSITION; CHIRALITY; CRYSTALLIZATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RACEMIC MIXTURE; SYNTHESIS;

EID: 27644568606     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.09.003     Document Type: Article

References (11)

1. Bolchi, C.; Di Pumpo, R.; Fumagalli, L.; Pallavicini, M.; Pedretti, A.; Valoti, E.; Villa, L.; Vistoli, G. Book of Abstracts, Joint Meeting on Medicinal Chemistry, Kraków, Poland, 15-18 October 2003, P129.
2. Bolchi, C.; Di Pumpo, R.; Fumagalli, L.; Mennini, T.; Pallavicini, M.; Pedretti, A.; Valoti, E.; Villa, L.; Vistoli, G. Atti del XVI Convegno Nazionale della Divisione di Chimica Farmaceutica della Società Chimica Italiana, Sorrento, 18-22 September 2002, L18.
3. A. Benarab, and G. Guillaumet Heterocycles 36 1993 2327
4. M. Soukri, S. Lazar, M. Akssira, and G. Guillaumet Org. Lett. 2 2000 1557
5. S. Lazar, M. Soukri, J.M. Leger, C. Jarry, M. Akssira, R. Chirita, I.C. Grig-Alexa, A. Finaru, and G. Guillaumet Tetrahedron 60 2004 6461
6. Van Emelen, K.; De Bruyn, M. F. L.; Alcázar-Vaca, M. J.; Andrés-Gil, J. I.; Fernández-Gadea, F. J.; Mattesanz-Ballesteros, M. E.; Bartolomé-Nebreda, J. M. WO0198306A1, 2001.
7. T. Kuppens, W. Langenaeker, J.P. Tollenaere, and P. Bultinck J. Phys. Chem. A 107 2003 542
8. C. Comoy, A. Benarab, A. Monteil, M. Leinot, R. Massingham, and G. Guillaumet Med. Chem. Res. 1996 392
9. M. Pallavicini, L. Villa, and E. Cesarotti J. Chromatogr. 604 1992 197
10. The best separation and resolution factors (α = 1.13, Rs = 0.8) were obtained on a Chiralcel OB column, eluting with hexane/ethanol/water 37.2:60.7:2.1 at 0.15 mL/min (mesyl ester of (R)-2: k′ = 1.65; mesyl ester of (S)-2: k′ = 1.87).
11. M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo Tetrahedron: Asymmetry 5 1994 5