Regio- and stereoselectivity of the formation of 1,3-oxazolidines in the reaction of l-ephedrine with phenylglyoxal. Unexpected rearrangement of 2-benzoyl-3,4-dimethyl-5-phenyl-1,3-oxazolidine to 4,5-dimethyl-3,6-diphenylmorpholin-2-one

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8223-8226

  Polyak, Felix ^a,b   Dorofeeva, Tatiana ^a   Zelchans, Gunars ^a   Shustov, Gennady ^a,c,d  

^a Latvian Academy of Sciences   (Latvia)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^c SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

^d UNIVERSITY OF PRINCE EDWARD ISLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MORPHOLINE DERIVATIVE; OXAZOLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030569295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01873-4     Document Type: Article

References (33)

1. 3. Ruxer, J.M.; Solladie, G J.Chem.Res.(S), 1978, 408-409. Just, G.; Luthe, C.; Potvin, P. Tetrahedron Lett. 1982, 23, 2285-2288. Moore, B.S.; Urban, F.J. U.S. US 5,149,821, 1992. C.A.1993.118, 147462r.
2. 3. Ruxer, J.M.; Solladie, G J.Chem.Res.(S), 1978, 408-409. Just, G.; Luthe, C.; Potvin, P. Tetrahedron Lett. 1982, 23, 2285-2288. Moore, B.S.; Urban, F.J. U.S. US 5,149,821, 1992. C.A.1993.118, 147462r.
3. 3. Ruxer, J.M.; Solladie, G J.Chem.Res.(S), 1978, 408-409. Just, G.; Luthe, C.; Potvin, P. Tetrahedron Lett. 1982, 23, 2285-2288. Moore, B.S.; Urban, F.J. U.S. US 5,149,821, 1992. C.A.1993.118, 147462r.
4. 4. For example, Scolastico, C. Pure & Appl.Chem., 1988, 60, 1689-1698 and references cited therein.
5. 5. Agami, C.; Couty, F. Tetrahedron Lett. 1987, 28, 5659-5660. Agami, C.; Meinier, F.; Rizk, T. Synth. Commun., 1987, 17, 241-250.
6. 5. Agami, C.; Couty, F. Tetrahedron Lett. 1987, 28, 5659-5660. Agami, C.; Meinier, F.; Rizk, T. Synth. Commun., 1987, 17, 241-250.
7. 6. Colombo, L.; Gennari, C.; Poli, G.; Scolastico, C. Tetrahedron Lett. 1985, 26, 5459-5462. Cardani, S.; Bernardi, A.; Colombo, L.; Gennari, C.; Scolastico, C.; Venturini, I. Tetrahedron, 1988, 44, 5563-5572.
8. 6. Colombo, L.; Gennari, C.; Poli, G.; Scolastico, C. Tetrahedron Lett. 1985, 26, 5459-5462. Cardani, S.; Bernardi, A.; Colombo, L.; Gennari, C.; Scolastico, C.; Venturini, I. Tetrahedron, 1988, 44, 5563-5572.
9. 7. Bernardi, A.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1989, 30, 3733-3734. Abdallah, H.; Gree, R.; Carrie. R. Tetrahedron Lett. 1982, 23, 503-506.
10. 7. Bernardi, A.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1989, 30, 3733-3734. Abdallah, H.; Gree, R.; Carrie. R. Tetrahedron Lett. 1982, 23, 503-506.
11. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
12. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
13. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
14. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
15. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
16. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
17. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
18. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
19. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
20. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
21. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
22. 8. Besace, Y.; Berlan, J.; Pourcelot, G.; Huche, M. J.Organomet.Chem. 1983, 247, C11-C13. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. J.Organomet.Chem. 1983, 256, 181-192. Berlan, J.; Besace, Y.; Prat, D.; Pourcelot, G. J.Organomet.Chem. 1984, 264, 399-408. Berlan, J.; Besace, Y.; Stephan, E.; Cresson, P. Tetrahedron Lett. 1985, 26, 5765-5768. Berlan, J.; Besace, Y.; Pourcelot, G.; Cresson, P. Tetrahedron, 1986, 42, 4757-4765. Berlan, J.; Besace, Y. Tetrahedron, 1986, 42, 4767-4776. Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1983, 24, 373-374. Bernardi, A.; Cardani, S.; Poli, G.; Scolastico, C. J.Org.Chem. 1986, 51, 5041-5043. Cardani, S.; Poli, G.; Scolastico, C.; Villa, R. Tetrahedron, 1988, 44, 5929-5938. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J.Org.Chem. 1988, 53, 1600-1607. Fleming, I.; Kingdom, N. J.Chem.Soc.Chem.Comm., 1987, 1177-1179. Alexakis, A.; Sedrani, R.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1988, 29, 4411-4414.
23. 9. Hussain, A.; Wyatt, P.B. Tetrahedron, 1993, 49, 2123-2130.
24. 10. Conde-Frieboes, K.; Hoppe, D. Tetrahedron, 1992, 48, 6011-6020.
25. 11. Gennari, C.; Poli, G.; Scolastico, C.; Vassalo, M. Tetrahedron: Asymmetry, 1991, 2, 793-796.
26. 12. Hoppe, I.; Hoppe, D.; Herbs-Irmer, R.; Egert, E. Tetrahedron Lett. 1990, 31, 6859-6862.
27. 13. Manzoni, L.; Pilati, T.; Poli, G.; Scolastico, C. J.Chem.Soc. Chem.Comm., 1992, 1027-1029.
28. 14. Polyak, F.; Solodin, I.; Dorofeeva, T. Synth. Comm. 1991, N10&11, 1137-1142.
29. 13.
30. 2= 6.5 Hz), 5.44 (1H, d, C5-H, J= 6.6 Hz), 5.57 (1H, s, C2-H), 7.13 - 7.60 (8H, m) and 8.13 (2H, d, J= 8.8 Hz) (protons of 2 benzene rings). Mass-spectrum (m/z; rel.int, %): 281(2.3) (M), 147 (25.7), 146 (44.3), 118 (100).
31. 17. Agami, C.; Rizk, T. Tetrahedron, 1985, 41, 537-540.
32. 2= 3.7 Hz), 4.11 (1H, s, C3-H), 5.44 (1H, d, C6-H, J= 3.7 Hz), 7.11 - 7.67 (10H, m, 2Ph). Mass-spectrum (m/z; rel.int., %): 281 (1.8) (M), 147 (25.5), 146 (45.5), 118 (100).
33. -3, F(000) = 568, room temperature, R = 0.062 for 1119 reflections.