Combining two-directional synthesis and tandem reactions, part 8: A novel condensation/Michael addition/cycloaddition/fragmentation/lactamisation cascade

Synlett

Volumn , Issue 14, 2006, Pages 2321-2324

  Sinclair, Alex ^a   Arini, Louise G ^a   Rejzek, Martin ^a   Szeto, Peter ^b   Stockman, Robert A ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Desymmetrisation; Elimination; Isooxazolidine; Ketolactam; Two directional

Indexed keywords

ISOOXAZOLIDINE; OXAZOLIDINE DERIVATIVE; OXIME; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; FRAGMENTATION REACTION; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; STEREOCHEMISTRY;

EID: 33748683557     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949634     Document Type: Article

References (11)

1. (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167.
2. (b) Poss, C.; Schreiber, S. Acc. Chem. Res. 1994, 24, 9.
3. Bruce, R. Tetrahedron 1995, 51, 13103.
4. For the previous paper in this series, see: Rejzek, M.; Stockman, R. A.; van Maarseveen, J. H.; Hughes, D. L. Chem. Commun. 2005, 4461.
5. (a) Stockman, R. A. Tetrahedron Lett. 2000, 41, 9163.
6. (b) Stockman, R. A.; Sinclair, A.; Arini, L. G.; Szeto, P.; Hughes, D. L. J. Org. Chem. 2004, 69, 1598.
7. Rejzek, M.; Stockman, R. A. Org. Biomol. Chem. 2005, 3, 73.
8. McDermott, P.; Stockman, R. A. Org. Lett. 2005, 7, 27.
9. Arini, L. G.; Szeto, P.; Hughes, D. L.; Stockman, R. A. Tetrahedron Lett. 2004, 45, 8371.
10. A similar epimerisation was reported by Holmes: Horsley, H. T.; Holmes, A. B.; Davies, J. E.; Goodman, J. M.; Silva, M. A.; Pascu, S. I.; Collins, I. Org. Biomol. Chem. 2004, 2, 1258.
11. Alexander, R.; Ko, E. C. F.; Parker, A. J.; Broxton, T. J. J. Am. Chem. Soc. 1968, 90, 5049.