Regioselective substitution of fluorine in F8BINOL as a versatile route to new ligands with axial chirality

Organic Letters

Volumn 2, Issue 22, 2000, Pages 3433-3436

  Chen, Yu ^a   Yekta, Shahla ^a   Martyn, L James P ^a   Zheng, Juan ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000321532     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006428k     Document Type: Article

References (47)

1. Jandeleit, B.; Schaefer, D. J.; Powers, T. S.; Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494.
2. For examples, see: (a) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
3. (b) Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475.
4. (c) Burgess, K.; Lim, H.-J.; Porte, A. M.; Sulikowski, G. A. Angew. Chem. Int. Ed. Engl. 1996, 35, 220.
5. (d) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668.
6. (e) VidalFerran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970.
7. (f) Shimizu, K. D.; Snapper, M. L.; Hoveyda, A. H. Chem. Eur. J. 1998, 4, 1885.
8. (g) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1988, 110, 4901.
9. (h) Gao, X.; Kagan, H. B. Chirality 1998, 10, 120.
10. (i) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Montalbetti, C. A. G. N.; Jackson, R. F. W. J. Org. Chem. 1998, 63, 5312.
11. (j) Taylor, S. J.; Morken, J. P. Science 1998, 280, 267.
12. (k) Boussie, T. R.; Coutard, C.; Turner, H. W.; Murphy, V.; Powers, T. S. Angew. Chem., Int. Ed. 1998, 37, 3272.
13. (l) Burgess, K.; Porte, A. M. Tetrahedron: Asymmetry 1998, 9, 2465.
14. (m) Reetz, M. T.; Becker, M. H.; Kuhling, K. M.; Holzwarth, A. Angew. Chem., Int. Ed. 1998, 37, 2647.
15. (n) Porte, A. M.; Reibenspiess, J.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 9180.
16. (o) Matsuo, J.; Odashima, K.; Kobayashi, S. Org. Lett. 1999, 1, 345.
17. (p) Reetz, M. T.; Becker, M. H.; Klein, H. W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758.
18. (q) Francis, M. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 937.
19. (r) LaPointe, A. M. J. Comb. Chem. 1999, 1, 101.
20. (s) Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225.
21. (t) Kobayashi, S. Curr. Opin. Chem. Biol. 2000, 4, 338.
22. (u) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279.
23. For representative applications of BINOL derivatives in asymmetric catalysis, see: (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
24. (b) Pu, L. Chem. Rev. 1998, 98, 2405.
25. (c) Rosini, C.; Franzini, L.; Rafaelli, A.; Salvadori, P. Synthesis 1992, 503.
26. (d) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
27. (e) Kitajima, H.; Katsuki, T. Synlett 1996, 568.
28. (f) Reetz, M. T.; Merk, C.; Naberfeld, G.; Rudolph, J.; Griebenow, N.; Goddard, R. Tetrahedron Lett. 1997, 38, 5273.
29. (g) Chan, A. S. C.; Zhang, F. Y.; Yip, C. W. J. Am. Chem. Soc. 1997, 119, 4080.
30. (h) Morita, T.; Arai, T.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1998, 9, 1445.
31. (i) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H.-G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223.
32. (j) Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220.
33. (k) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Curran, D. P. Tetrahedron 2000, 56, 351.
34. (l) Ishitani, H.; Yamashita, Y.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 5403.
35. Yudin, A. K.; Martyn, L. J. P.; Pandiaraju, S.; Zheng, J.; Lough, A. Org. Lett. 2000, 2, 41.
36. Martyn, L. J. P.; Pandiaraju, S.; Yudin, A. K. J. Organomet. Chem. 2000, 603, 98.
37. Welch, J. T.; Peters, D.; Miethchen, R.; Il'chenko, A. Y.; Rüdiger, S.; Podlech, J. In Organo-fluorine Compounds, 4th ed.; Baasner, B., Hagemann, H., Tatlow, J. C., Eds.; Georg Thieme Verlag: Stuttgart, 2000; Vol. E10b/Part 2, pp 293-459.
38. o)]. The data that were collected on a Nonius Kappa-CCD were integrated and scaled using the DENZO-SMN package (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326). The structures were solved and refined using SHELXTL V5.0 (Sheldrick, G. M. SHELXTL\PC V5.1, Bruker Analytical X-ray Systems, Madison, WI, 1997).
39. o)]. The data that were collected on a Nonius Kappa-CCD were integrated and scaled using the DENZO-SMN package (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326). The structures were solved and refined using SHELXTL V5.0 (Sheldrick, G. M. SHELXTL\PC V5.1, Bruker Analytical X-ray Systems, Madison, WI, 1997).
40. For examples, see: (a) Chow, H. F.; Ng, M. K. Tetrahedron: Asymmetry 1996, 7, 2251.
41. (b) Ng, M.-K.; Chow, H.-F. Tetrahedron Lett. 1996, 37, 2979.
42. (c) Zhang, F. Y.; Yip, C. W.; Cao, R.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 585.
43. (d) Mori, M.; Nakai, T. Tetrahedron Lett 1997, 38, 6233.
44. (e) Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295.
45. (f) Yang, X. W.; Su, W.; Liu, D. X.; Wang, H. S.; Shen, J. H.; Da, C. S.; Wang, R.; Chan, A. S. C. Tetrahedron 2000, 56, 3511.
46. (g) Nakamura, Y.; Takeuchi, S.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 2000, 41, 57.
47. Studies aimed at understanding the effect of remote substitution on kinetic resolution of sulfoxides in this system are in progress.