Synthesis of 2,6-disubstituted morpholines through regioselective oxiranes ring opening by tosylamide under PTC conditions

Tetrahedron

Volumn 60, Issue 51, 2004, Pages 11709-11718

  Lupi, Vittoria ^a   Albanese, Domenico ^a   Landini, Dario ^a   Scaletti, Davide ^a   Penso, Michele ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR Consiglio Nazionale delle Ricerche   (Italy)

Author keywords

Cyclization; Morpholines; Oxirane ring opening; Phase transfer catalysis

Indexed keywords

AGRICULTURAL CHEMICAL; ETHYLENE OXIDE DERIVATIVE; MORPHOLINE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DEPROTECTION REACTION; DRUG SYNTHESIS; LIQUID; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SOLID;

EID: 8444232793     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.10.008     Document Type: Article

References (27)

1. B.A. Lanman, and A.G. Myers Org. Lett. 6 2004 1045 1047
2. R. Dave, and N.A. Sasaki Org. Lett. 6 2004 15 18
3. Meki, N.; Takano, J. JP 01254680; Chem. Abstr. 1990, 112, 179000.
4. Antony, V. M.; Worthington, P. A. EP 253498; Chem. Abstr. 1988, 109, 6529.
5. Camaggi, G.; Filippini, L.; Gusmeroli, M.; Riva, R.; Garavaglia, C.; Mirenna, L. EP 521465; Chem. Abstr. 1993, 118, 212675.
6. Carson, C. M.; Copping, L. G.; Ehr, R. J.; Gitlitz, M. H.; McNeil, M. W.; Street, P. F. S.; Liebeschuetz, M. H. EP 313353; Chem. Abstr. 1989, 111, 154100.
7. Meki, N.; Takano, H. EP 262870; Chem. Abstr. 1989, 110, 192837.
8. C.R. Worthing The Pesticide Manual 7th ed. 1983 British Crop Protection Council pp 265, 550
9. R. Wegler Chemie der Pflanzenschutz- und Schädlingsbekä mpfungsmittel 1970 Springer Berlin Vol. 2, p 123
10. R. Wegler Chemie der Pflanzenschutz- und Schädlingsbekä mpfungsmittel 1977 Springer Berlin Vol. 4, p 219
11. W.S. Bowers, W. Ebing, T.R. Fukuto, and D. Martin Chemistry of Plant Protection 1986 Springer Berlin Vol. 1, pp 55-56
12. E. Licandro, S. Maiorana, A. Papagni, M. Pryce, A. Zanotti-Gerosa, and S. Riva Tetrahedron: Asymmetry 6 1995 1891 1894
13. C. Baldoli, P. Del Buttero, E. Licandro, S. Maiorana, S. Papagni, and A. Zanotti-Gerosa J. Organomet. Chem. 486 1995 279 282
14. Hikichi, M.; Yokokura, T.; Furuta, T.; Yaegashi, T. JP 62135472; Chem. Abstr. 1987, 107, 198358.
15. GB 831933; Chem. Abstr. 1961, 55, 2697.
16. Sharma, M. M. BE 660875; Chem. Abstr. 1966, 64, 33470.
17. Scott, C. R.; Ayers, A. L.; Mahan, J. E. US 2771737; Chem. Abstr. 1957, 51, 19438.
18. Kotaka, N.; Saito, R.; Motokawa, N. JP 02111765; Chem. Abstr. 1990, 113, 132199.
19. Tanaka, K. JP 01313576; Chem. Abstr. 1990, 112, 237012.
20. Sanne, W.; Koenig, K. H.; Pommer, H.; Stummeyer, H. BE 614214; Chem. Abstr. 1963, 58, 27366.
21. Payman, J. B., Piggot, H. A. GB 298336; Chem. Abstr. 1929, 23, 22918.
22. Payman, J. B.; Piggot, H. A. US 1859527; Chem. Abstr. 1932, 26, 36615.
23. G. Bettoni, C. Franchini, R. Perrone, and V. Tortorella Tetrahedron 36 1980 409 415
24. S. Hernestam J. Heterocycl. Chem. 20 1983 1681 1685
25. Langdon, W. K.; Ernest, J.; Levis, W. W., Jr. GB 835717; Chem. Abstr. 1961, 55, 13519.
26. D. Albanese, D. Landini, M. Penso, and S. Petricci Tetrahedron 55 1999 6387 6394
27. G. Li, and K.B. Sharpless Acta Chem. Scand. 50 1996 649 651