A first case of asymmetric catalysis induced by metal-free bisoxazolines

European Journal of Organic Chemistry

Volumn , Issue 14, 2008, Pages 2365-2368

  Akalay, Deniz ^a   Dürner, Gerd ^a   Göbel, Michael W ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

Asymmetric catalysis; Bisoxazolines; Cycloaddition; Enantioselectivity; Organocatalysis

Indexed keywords

EID: 53749086312     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800179     Document Type: Article

References (28)

1. D. Akalay, G. Dürner, J. W. Bats, M. Bolte, M. W. Göbel, J. Org. Chem. 2007, 72, 5618-5624.
2. a) M. Koerner, B. Rickborn, J. Org. Chem. 1989, 54, 6-9;
3. b) M. Koerner, B. Rickborn, J. Org. Chem. 1990, 55, 2662-2672;
4. c) O. Riant, H. B. Kagan, Tetrahedron Lett. 1989, 30, 7403-7406;
5. d) O. Riant, H. B. Kagan, Tetrahedron 1994, 50, 4543-4554;
6. e) R. Harrison, B. Rickborn, Org. Lett. 2002, 4, 1711-1713.
7. F. Fache, O. Piva, Tetrahedron Lett. 2001, 42, 5655-5657.
8. a) K. Uemae, S. Masuda, Y. Yamamoto, J. Chem. Soc. Perkin Trans. 1 2001, 1002-1006;
9. b) K. Tokioka, S. Masuda, T. Fujii, Y. Hata, Y. Yamamoto, Tetrahedron: Asymmetry 1997, 8, 101-107.
10. J. Shen, T. Nguyen, Y. P. Goh, W. Ye, X. Fu, C. H. Tan, J. Am. Chem. Soc. 2006, 128, 13692-13693.
11. a) For an excellent review see: G. Dimoni, G. Faita, K. A. Jørgensen, Chem. Rev. 2006, 106, 3561-3651;
12. b) S. Nakamura, N. Hirata, T. Kita, R. Yamada, D. Nakane, N. Shibata, T. Toru, Angew. Chem. Int. Ed. 2007, 46, 7648-7650.
13. Corey et al. reported on a control experiment involving 8a, TMSCN and cyclohexane carboxaldehyde to give completely racemic cyanohydrin TMS ether by forming a complex with a chiral cyanide-donor-derived from bisoxazoline: E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4003.
14. 3) corresponds for 61% ee, K. Uemae, S. Masuda, Y. Yamamoto, J. Chem. Soc. Perkin Trans. 1 2001, 1002-1006.
15. a) H. O. House, J. A. Hrabie, D. VanDerveer, J. Org. Chem. 1986, 51, 921-929;
16. b) H. Prinz, W. Wiegrebe, K. Müller, J. Org. Chem. 1996, 61, 2853-2856.
17. M. A. Walker, J. Org. Chem. 1995, 60, 5352-5355.
18. M. P. Cava, A. A. Deana, K. Muth, M. J. Mitchell, Org. Synth. 1961, 41, 93-95.
19. a) R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6008;
20. b) M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 1996, 118, 8489-8490;
21. c) V. Schulze, R. W. Hoffmann, Chem. Eur. J. 1999, 5, 337-344;
22. d) J. M. Atkins, S. A. Moteki, S. G. DiMagno, J. M. Takacs, Org. Lett. 2006, 8, 2759-2762.
23. a) H. Fritschi, U. Leutenegger, A. Pfaltz, Angew. Chem. Int. Ed. Engl. 1986, 25, 1005-1006;
24. b) H. Fritschi, U. Leutenegger, K. Siegmann, A. Pfaltz, W. Keller, C. Cratky, Helv. Chim. Acta 1988, 71, 1541-1552;
25. c) H. Fritschi, U. Leutenegger, A. Pfaltz, Helv. Chim. Acta 1988, 71, 1553-1565;
26. d) U. Leutenegger, A. Madin, A. Pfaltz, Angew. Chem. Int. Ed. Engl. 1989, 28, 60-61;
27. e) D. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232-240.
28. B. Kovač, L. Klasinc, Z. Raza, V. Šunjić, J. Chem. Soc. Perkin Trans. 2 1999, 2455-2459.