A new, stereoselective approach to pyrrolidine-N-oxides by sequential condensation of sulfones with nitrones and reverse-cope elimination

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8553-8556

  Wheildon, Andrew R ^a   Knight, David W ^b   Leese, Mathew P ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030660638     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10245-3     Document Type: Article

References (8)

1. Coogan, M.P.; Gravestock, M.B.; Knight, D.W.; Thornton, S.R. Tetrahedron Lett., 1997, 38, 8549.
2. Chang, Z.-Y.; Coates, R.M. J. Org. Chem., 1990, 55, 3464 and references cited therein.
3. Ciganek, E. J. Org. Chem., 1990, 55, 3007; 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795 and references cited therein.
4. Ciganek, E. J. Org. Chem., 1990, 55, 3007; 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795 and references cited therein.
5. Ciganek, E. J. Org. Chem., 1990, 55, 3007; 1995, 60, 5803; Ciganek, E.; Read, J.M.; Calabrese, J.C. J. Org. Chem., 1995, 60, 5795 and references cited therein.
6. Breuer, E.; Aurich, H.G.; Nielsen, A. "Nitrones, Nitronates and Nitroxides, Eds. Patai, S; Rappoport, Z., John Wiley and Sons, Chichester, 1989.
7. For an isolated example of the addition of a lithiated sulfone to a nitrone, see Annunziata, R.; Cinquini, M. Synthesis, 1982, 929.
8. For an alternative approaches to pyrrolidine-N-oxides, see O'Neil, I.A.; Miller, N.D.; Barkley, J.V.; Low, C.M.R.; Kalindjian, S.B. Synlett, 1995, 617, 619.