Stereoselective access to trans-2,5-disubstituted pyrrolidine derivatives by nucleophilic addition to bicyclic N-acyliminium ion

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1415-1418

  Dhimane, Hamid ^a   Vanucci, Corinne ^a   Lhommet, Gérard ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584886     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00099-3     Document Type: Article

References (12)

1. 1. (a) Wistrand, L.G.; Skrinjar, M. Tetrahedron, 1991, 47, 573-582;
2. (b) Langlois, N.; Rojas, A. Tetrahedron 1993, 49, 77-82;.
3. (c) Collado, I.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 1995, 60, 5011-5015;
4. (d) Chiesa, M.V.; Manzoni, L.; Scolastico, C. Synlett 1996, 441-443.
5. 2. Shono, T.; Fujita, T.; Matsumura, Y. Chem. Letters, 1991, 81, 80-84.
6. 3. (a) Agami, C.; Couty, F.; Hamon, L.; Venier, O. Tetrahedron Lett. 1993, 34, 4509-4512;
7. (b) Curran, T.P.; Pallastri, M.P.; Abelleira, S.M.; Messier, R.J.; McCollum, T.A.; Rowe, C.G. Tetrahedron Lett. 1994, 35, 5409-5412.
8. 2O at reflux) then TsCl in pyridine.
9. 5. A similar regioselectivity was observed in the case of bicyclic oxazinones : Driessens, F.; Hootele, C. Can. J. Chem. 1990, 211.
10. 6. Rosset, S.; Célérier, J.P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 7521-7525.
11. 7. Pedregal, C.; Ezquerra, J.; Escribano, A.; Carreno, M.C.; Garcia Ruano, J.L. Tetrahedron Lett., 1994, 35, 2053-2056.
12. 2 was converted into oxazolidinones in three steps according to the following scheme : (formula presented)