Efficient π-facial control in the ene reaction of nitrosoarene, triazolinedione, and singlet oxygen with tiglic amides of the bornane-derived sultam as chiral auxiliary: An economical synthesis of enantiomerically pure nitrogen- and oxygen-functionalized acrylic acid derivatives

Journal of the American Chemical Society

Volumn 124, Issue 44, 2002, Pages 12938-12939

  Adam, Waldemar ^a   Degen, Hans Georg ^a   Krebs, Oliver ^a   Saha Möller, Chantu R ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; AMIDE; BORNANE DERIVATIVE; NITROGEN; NITROSO DERIVATIVE; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; OPTICAL ROTATION; STEREOCHEMISTRY; SYNTHESIS;

ACRYLATES; ALKENES; AMINO ACIDS; BORNANES; NITROSO COMPOUNDS; SINGLET OXYGEN; STEREOISOMERISM; TRIAZOLES;

EID: 0037032210     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026640e     Document Type: Article

References (29)

1. (a) Clennan, E. L. Tetrahedron 2000, 56, 9151-9179.
2. (b) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708.
3. (a) Adam, W.; Bottke, N.; Krebs, O. J. Am. Chem. Soc. 2000, 122, 6791-6792.
4. (b) Adam, W.; Bottke, N.; Krebs, O.; Engels, B. J. Am. Chem. Soc. 2001, 123, 5542-5548.
5. Adam, W.; Bottke, N. J. Am. Chem. Soc. 2000, 122, 9846-9847.
6. Adam, W.; Bottke, N.; Krebs, O.; Saha-Möller, C. R. Eur. J. Org. Chem. 1999, 1963-1965.
7. (a) Jones, S. J. Chem. Soc., Perkin Trans. 1 2002, 1-21.
8. (b) Adam, W.; Peters, K.; Schambony, S. B. J. Am. Chem. Soc. 2000, 122, 7610-7611.
9. (c) Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293-318.
10. (a) Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913-945.
11. (b) Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
12. (c) Gademann, K.; Seebach, D. Helv. Chim. Acta 2001, 84, 2924-2937.
13. (a) Smith, M. B. Methods of Non-α-Amino Acid Synthesis; Marcel Dekker: New York, 1995.
14. (b) Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997.
15. (a) Oppolzer, W.: Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G. Helv. Chim. Acta 1987, 70. 2201-2214.
16. (b) Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1984, 23, 876-890.
17. (a) Adam, W.; Wirth, T.; Pastor, A.; Peters, K. Eur. J. Org. Chem. 1998, 501-506.
18. (b) Wirth, T. Dissertation, University of Würzburg, 1998.
19. (a) Adam, W.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1737-1739.
20. (b) Adam, W.; Fell, R. T.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1995, 6, 1047-1050.
21. (c) Hoch, U. Dissertation, University of Würzburg, 1996.
22. Drewes, S. E.; Hoole, R. F. A. Synth. Commun. 1985, 15, 1067-1074.
23. Adam, W.; Groer, P.; Saha-Möller, C. R. J. Org. Chem. 2000, 65, 4919-4922.
24. Groer, P. Dissertation. University of Würzburg, 2000.
25. Zyss, J.; Nicoud, J. F. J. Chem. Phys. 1984, 81, 4160-4167.
26. Oppolzer, W.; Poli, G.; Starkemann, C.; Bernardinelli, G. Tetrahedron Lett. 1988, 29, 3559-3562.
27. Since only one stereogenic center is formed in these ene reactions, namely at the β position of the CC double bond. the descriptor for the π-face attack refers to the β-carbon atom.
28. Curran, D. P.; Kim, B. H.; Daugherty, J.; Heffner, T. A. Tetrahedron Lett. 1988, 29, 3555-3558.
29. Curran, D. P.; Heffner, T. A. J. Org. Chem. 1990, 55, 4585-4595.