A practical approach to the synthesis of enantiomerically pure 2,6-disubstituted morpholines under phase transfer catalysis conditions

Catalysis Today

Volumn 140, Issue 1-2, 2009, Pages 100-104

  Albanese, D ^a   Foschi, F ^a   Penso, M ^b  

^a Dipartimento di Chimica Organica e Industriale   (Italy)

^b CNR   (Italy)

Author keywords

Cyclization; Morpholines; Phase transfer catalysis; Sulfonamides

Indexed keywords

AMIDES; CYCLIZATION; PLATINUM COMPOUNDS; SULFUR COMPOUNDS;

CHIRAL EPOXIDES; HIGH YIELDING; LIQUID PHASE; MORPHOLINES; PHASE TRANSFER CATALYSIS; PHASE TRANSFER CATALYSIS CONDITIONS; REGIOSELECTIVE; RING OPENINGS; SULFONAMIDES; SYNTHESIS OF;

CATALYSIS;

EID: 57849165735     PISSN: 09205861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cattod.2008.07.005     Document Type: Article

References (18)

1. For recent examples: (a) B.A. Lanman, A.G. Myers, Org. Lett. 6 (2004) 1045; (b) K. Audouze, Ø.E. Nielsen, D. Peters, J. Med. Chem. 47 (2004) 3089; (c) R. Wijtmans, M.K.S. Vink, H.E. Schoemaker, F.L. van Delft, R.H. Blaauw, F.P.J.T. Rutjes, Synthesis (2004) 641.
2. Forsyth S.A., Gunaratne H.Q.N., Hardacre C., McKeown A., and Rooney D.W. Org. Process Res. Dev. 10 (2006) 94
3. Uozumi Y., Tanahashi A., and Hayashi T. J. Org. Chem. 58 (1993) 6826
4. Yamazaki A., and Achiwa K. Tetrahedron: Asymmetry 5 (1995) 1021
5. Thorey C., Wilken J., Hénin F., Martens J., Mehler T., and Muzart J. Tetrahedron Lett. 36 (1995) 5527
6. Ito K., Imahayashi Y., Kuroda T., Eno S., Saito B., and Katsuki T. Tetrahedron Lett. 45 (2004) 7277
7. Massacret M., Lakhmiri R., Lhoste P., Nguefack C., Abdelouahab F.B.B., Fadel R., and Sinou D. Tetrahedron: Asymmetry 11 (2000) 3561
8. Wilkinson M.C. Tetrahedron Lett. 46 (2005) 4773
9. Nakano H., Yokoyama J.-I., Fujita R., and Hongo H. Tetrahedron Lett. 43 (2002) 7761
10. Bouron E., Goussard G., Marchand C., Bonin M., Pannecoucke X., Quirion J.-C., and Husson H.-P. Tetrahedron Lett. 40 (1999) 7227
11. Enders D., Meyer O., Raabe G., and Runsink J. Synthesis (1993) 66
12. Baldoli C., Del Buttero P., Licandro E., Maiorana S., Papagni A., and Zanotti Gerosa A. J. Organomet. Chem. 486 (1995) 279
13. Licandro E., Maiorana S., Capella L., Manzotti R., Papagni A., Pryce M., Graiff C., and Tiripicchio A. Eur. J. Org. Chem. (1998) 2127
14. Dave R., and Sasaki N.A. Tetrahedron: Asymmetry 17 (2006) 388
15. Albanese D., Salsa M., Landini D., Lupi V., and Penso M. Eur. J. Org. Chem. (2007) 2107
16. Baldwin J.E. Chem. Commun. (1976) 734
17. Lepine R., Carbonnelle A.-C., and Zhu J. Synlett (2003) 1455
18. Gibson F.S., Park M.S., and Rapoport H. J. Org. Chem. 59 (1994) 7503