CBS oxazaborolidines - Versatile catalysts for asymmetric synthesis

Synlett

Volumn , Issue 6, 2007, Pages 997-998

  Stemmler, René T ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZABOROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; OZONOLYSIS;

EID: 34247141414     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-973876     Document Type: Article

References (34)

1. For reviews, see: (a) Cho, B. T. Tetrahedron 2006, 62, 7621.
2. (b) Cho, B. T. Aldrichimica Acta 2002, 35, 3.
3. (c) Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37, 1986;
4. Angew. Chem. 1998, 110, 2092.
5. (d) Itsuno, S. Org. React. 1998, 52, 395.
6. CBS represents the initials of the researchers who discovered the reagents 1a-c, namely Corey, Bakshi, and Shibata: (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
7. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
8. (a) Demir, A. S.; Sesenoglu, Ö.; Ülkü, D.; Arici, C. Helv. Chim. Acta 2003, 86, 91.
9. (b) Demir, A. S.; Sesenoglu, Ö.; Aksoy-Cam, H.; Kaya, H.; Aydogan, K. Tetrahedron: Asymmetry 2003, 14, 1335.
10. (c) Demir, A. S.; Sesenoglu, Ö.; Gerçek-Arkin, Z. Tetrahedron: Asymmetry 2001, 12, 2309.
11. (a) Gosselin, F.; O'Shea, P. D.; Roy, S.; Reamer, R. A.; Chen, C.-y.; Volante, R. P. Org. Lett. 2005, 7, 355.
12. (b) Kirton, E. H. M.; Tughan, G.; Morris, R. E.; Field, R. A. Tetrahedron Lett. 2004, 45, 853.
13. Uenishi, J.; Ohmi, M. Angew. Chem. Int. Ed. 2005, 44, 2756;
14. Angew. Chem. 2005, 117, 2816.
15. Matsuo, G.; Kawamura, K.; Hori, N.; Matsukura, H.; Nakata, T. J. Am. Chem. Soc. 2004, 126, 14374.
16. Kita, Y.; Matsuda, S.; Fujii, E.; Horai, M.; Hata, K.; Fujioka, H. Angew. Chem. Int. Ed. 2005, 44, 5857;
17. Angew. Chem. 2005, 117, 6007.
18. Crimmins, M. T.; DeBaillie, A. C. J. Am. Chem. Soc. 2006, 128, 4936.
19. (a) Molander, G. A.; George, K. M.; Monovich, L. G. J. Org. Chem. 2003, 68, 9533.
20. (b) Bringmann, G.; Pabst, T.; Henschel, P.; Kraus, J.; Peters, K.; Peters, E.-M.; Rycroft, D. S.; Connolly, J. D. J. Am. Chem. Soc. 2000, 122, 9127.
21. (a) Abe, H.; Takeda, S.; Fujita, T.; Nishioka, K.; Takeuchi, Y.; Harayama, T. Tetrahedron Lett. 2004, 45, 2327.
22. (b) Bringmann, G.; Menche, D.; Kraus, J.; Mühlbacher, J.; Peters, K.; Peters, E.-M.; Brun, R.; Bezabih, M.; Abegaz, B. M. J. Org. Chem. 2002, 67, 5595.
23. (c) Bringmann, G.; Ochse, M.; Götz, R. J. Org. Chem. 2000, 65, 2069.
24. For a review, see: Bolm, C.; Rantanen, T.; Schiffers, I.; Zani, L. Angew. Chem. Int. Ed. 2005, 44, 1758;
25. Angew. Chem. 2005, 117, 1788.
26. (a) Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 1346.
27. (b) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
28. (c) Zhou, G.; Hu, Q.-Y.; Corey, E. J. Org. Lett. 2003, 5, 3979.
29. (d) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808.
30. (e) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992.
31. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106.
32. Liu, D.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 8160.
33. Boeckman, R. K. Jr.; Pero, J. E.; Boehmler, D. J. J. Am. Chem. Soc. 2006, 128, 11032.
34. Compounds (S)-1b, (R)-1b, and (S)-o-tolyl-CBS-oxazaborolidine are commercially available.