Chemo-enzymatic synthesis of the active enantiomer of the anorressant 2- benzylmorpholine

Tetrahedron Asymmetry

Volumn 9, Issue 22, 1998, Pages 4021-4026

  D'Arrigo, Paola ^a   Lattanzio, Maria ^a   Fantoni, Giuseppe Pedrocchi ^a   Servi, Stefano ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 2 PROPANOL; 2 BENZYLMORPHOLINE; ALPHA BROMOCINNAMALDEHYDE; EPOXIDE; STYRENE OXIDE; UNCLASSIFIED DRUG;

APPETITE; ARTICLE; CATALYST; ENANTIOMER; ENZYME SYNTHESIS; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY;

EID: 0032573612     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00432-7     Document Type: Article

References (30)

1. Simon, H.; Bader, J.; Günther, H.; Neumann, S.; Thanos, J. Angew. Chem., Int. Ed. Eng. 1985, 24, 539.
2. Belan, A.; Bolte, J.; Fauve, A.; Gourcy, J. G.; Veschambre, H. J. Org. Chem. 1987, 54, 256.
3. Leunberger, H. G. W.; Boguth, W.; Widmer, E.; Zell, R. Helv. Chim. Acta 1976, 59, 1832.
4. Fuganti, C.; Ghiringhelli, D.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1975, 846.
5. Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1988, 44, 1299.
6. Högberg, H. E.; Hedenström, E.; Fägerhag, J; Servi, S. J. Org. Chem. 1992, 57, 2052.
7. Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1987, 43, 4481.
8. Sato, T.; Hanayama, K.; Fujisawa, T. Tetrahedron Lett. 1988, 29, 2197.
9. Ohta, H.; Kobayashi, A.; Ozaki, K. J. Org. Chem. 1989, 54, 1802.
10. Zueger, M. F.; Giovannini, F.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 12, 1012.
11. Goodhue, C. T.; Schaffer, J. R. Biotechnol. Bioeng. 1971, 13, 203.
12. Utaka, M.; Konishi, S.; Okubo, T.; Tsuboi, S.; Takeda, A. Tetrahedron Lett. 1987, 28, 1447.
13. Leunberger, H. G. W. In Biocatalysts in Organic Synthesis; Tramper, J.; Van der Plas, H. C.; Linko, P., Eds; Elsevier: Amsterdam, 1985; p. 99.
14. Koul, S.; Crout, D. H. G.; Errington, W.; Tax, J. J. Chem. Soc., Chem. Commun. 1995, 2969.
15. Fuganti, C.; Pedrocchi Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135.
16. Fronza, G.; Fogliato, G.; Fuganti, C.; Lanati, S.; Rallo, R.; Servi, S. Tetrahedron Lett. 1995, 36, 123.
17. Utaka, M.; Konishi, S.; Takeda, A. Tetrahedron Lett. 1986, 27, 4737.
18. Kobayashi, H. Recl. Trav. Chim. Pays-Bas 1996, 115, 201.
19. Buendia, J.; Crocq, V.; Masson, C.; Prat, D.; Vivat, M. Eur. Pat. Appl. 574,317, 1993.
20. Crocq, V.; Masson, C.; Winter, J.; Richard, C.; Lemaitre, G.; Lenay, J.; Vivat, M.; Buendia, J.; Prat, D. Organic Process R&D 1997, 1, 2.
21. Fuganti, C.; Grasselli, P.; Servi, S.; Högberg, H. E. J. Chem. Soc., Perkins Trans. 1 1988, 1061.
22. D'Arrigo, P.; Pedrocchi Fantoni, G.; Servi, S.; Strini, A. Tetrahedron: Asymmetry 1997, 8, 2375-2379.
23. Brown, G. R.; Forster, G.; Foubister, A. J.; Stribling, D. J. Pharm. Pharmacol. 1990, 42, 797-799.
24. Fuganti, C.; Grasselli, P. Chem. Ind. (London) 1977, 983.
25. Chen, C. S.; Zhou, B. N.; Girdaukas, G.; Shieh, W. R.; VanMiddlesworth, F.; Gopalan, A. S.; Sih, C. J. Bioorg. Chem. 1984, 12, 98-117.
26. Nakamura, K., Kondo, S.-I.; Nakajima, N.; Ohno, A. Tetrahedron 1995, 51, 687.
27. D'Arrigo, P.; Fuganti, C.; Pedrocchi Fantoni, G.; Servi, S. Tetrahedron 1998, 54, 15017-15026.
28. Arens, C. L.; Hallgarten, P. A. J. Chem. Soc. 1956, 2987-2990.
29. Koppenhoefer, B.; Schurig, V Org. Synth. 1987, 66, 151.
30. Bradshaw, J. S.; Huszthy, P.; McDaniel, C. W.; Zhu, C. Y.; Kent-Dalley, N.; Izatt, R. M.; Lifson, S. J. Org. Chem. 1990, 55, 3129-3137.