Investigation of Lewis Acid-Catalyzed Asymmetric Aza-Diels-Alder Reactions of 2H-Azirines

Journal of Organic Chemistry

Volumn 68, Issue 26, 2003, Pages 9958-9963

  Timén, Åsa Sjöholm ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVITY;

CARBOXYLATION; CATALYSIS; SUBSTITUTION REACTIONS;

STEREOCHEMISTRY;

2H AZIRINE DERIVATIVE; 3 BENZYL 2H AZIRINE CARBOXYLATE; AZIRINE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; HETEROCYCLIC COMPOUND; LEWIS ACID; PYRIDINE DERIVATIVE; TETRAHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZIRINES; CATALYSIS; CYCLOPENTANES; HYDROGEN-ION CONCENTRATION; PYRIDINES; STEREOISOMERISM;

EID: 0346362507     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0352326     Document Type: Article

References (31)

1. Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications, 3rd ed.; Thieme: Würtsburg, Germany, 1999.
2. Ojima, I. Catalytic asymmetric synthesis; VCH Publishers: New York, 1993.
3. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995.
4. Oppolzer, W. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 316-399.
5. (a) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
6. (b) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
7. Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder methodology in organic synthesis; Academic Press: New York, 1987; Vol. 47.
8. Buonora, P.; J.-C., O.; Oh, T. Tetrahedron 2001, 57, 6099-6138.
9. Weinreb, S. M. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 401-449.
10. Anderson, D. J.; Hassner, A. Synthesis 1975, 483-495.
11. Gilchrist, T. L. Aldrichim. Acta 2001, 34, 51-55.
12. Davis, F. A.; Wu, Y.; Yan, H.; Prasad, K. R.; McCoull, W. Org. Lett. 2002, 4, 655-658.
13. Bickley, J. F.; Gilchrist, T. L.; Mendonca, R. Arkivoc 2002, 192-204.
14. (a) Álvares, Y. S. P.; Alves, M. J.; Azoia, N. G.; Bickley, J. F. ; Gilchrist, T. L. J. Chem. Soc., Perin Trans. 1 2002, 1911-1919.
15. (b) Gilchrist, T. L.; Mendonça, R. Arkivoc 2000, 1, 769-778.
16. Ray, C. A.; Risberg, E.; Somfai, P. Tetrahedron 2002, 58, 5983-5987.
17. Ray, C. A.; Risberg, E.; Somfai, P. Tetrahedron Lett. 2001, 42, 9289-9291.
18. Sjöholm Timén, Å.; Fischer, A.; Somfai, P. Chem. Commun. 2003, 1150-1151.
19. Motoyama, Y.; Nishiyama, H. In Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2000; Vol. 1, p 59-88.
20. The absolute configuration of 3a and 4a has not been determined.
21. 4 were screened.
22. Mayr, H.; Striepe, W. J. Org. Chem. 1985, 50, 2995-2998.
23. Alcami, M.; Mó, O.; Yánez, M. J. Am. Chem. Soc. 1993, 115, 11074-11083.
24. Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667.
25. Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558-3588.
26. Azirine 15 was prepared by thermolysis from the corresponding vinyl azide.27 The vinyl azide was obtained in two steps, using a slightly modified literature procedure, starting from benzyl acrylate. Gilchrist, T. L.; Mendonca, R. Synlett 2000, 1843-1845.
27. Cernerud, M.; Skrinning, A.; Bérgère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437-3441.
28. Loss of product was observed on both silica and aluminum oxide.
29. Sjöholm Timén, Å.; Risberg, E.; Somfai, P. Tetrahedron Lett. 2003, 44, 5339-5341.
30. Thom, C.; Kocienski, P. Synthesis 1992, 582-586.
31. Whitesell, J. K.; Liu, C.-L.; Buchanan, C. M.; Chen, H.-H.; Minton, M. A. J. Org. Chem. 1986, 51, 551-553.