Generation of chiral boron enolates by rhodium-catalyzed asymmetric 1,4-addition of 9-aryl-9-borabicyclo[3.3.1]nonanes (B-Ar-9BBN) to α,β-unsaturated ketones

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1901-1905

  Yoshida, Kazuhiro ^a   Ogasawara, Masamichi ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILES;

ADDITION REACTIONS; BORON; CATALYSIS; METHANOL; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

TOLUENE;

2 CYCLOHEXENONE; 9 BORABICYCLO[3.3.1]NONANE DERIVATIVE; BORON DERIVATIVE; BROMINE DERIVATIVE; KETONE DERIVATIVE; METHANOL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPANOL; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY;

EID: 0037424526     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020659i     Document Type: Article

References (37)

1. (a) For recent reviews: Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
2. (b) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
3. (c) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; Vol. 3, Chapter 31.1.
4. (d) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; pp 569-592.
5. (e) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; pp 207-212.
6. Recent examples of copper-catalyzed asymmetric 1,4-addition of organozinc reagents with high enantioselectivity: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262. (c) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841. (d) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (e) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755. (f) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879.
7. Recent examples of copper-catalyzed asymmetric 1,4-addition of organozinc reagents with high enantioselectivity: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262. (c) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841. (d) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (e) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755. (f) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879.
8. Recent examples of copper-catalyzed asymmetric 1,4-addition of organozinc reagents with high enantioselectivity: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262. (c) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841. (d) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (e) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755. (f) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879.
9. Recent examples of copper-catalyzed asymmetric 1,4-addition of organozinc reagents with high enantioselectivity: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262. (c) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841. (d) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (e) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755. (f) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879.
10. Recent examples of copper-catalyzed asymmetric 1,4-addition of organozinc reagents with high enantioselectivity: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262. (c) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841. (d) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (e) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755. (f) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879.
11. Recent examples of copper-catalyzed asymmetric 1,4-addition of organozinc reagents with high enantioselectivity: (a) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262. (c) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841. (d) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358. (e) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755. (f) Escher, I. H.; Pfaltz, A. Tetrahedron 2000, 56, 2879.
12. (a) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
13. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479.
14. (c) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047.
15. (d) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957.
16. (e) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591.
17. (f) Takaya, Y.; Ogasawara, M.; Hayashi, T. Chirality 2000, 12, 469.
18. (g) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
19. (h) Hayashi, T. Synlett 2001, 879.
20. (i) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852.
21. (a) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
22. (b) Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944.
23. (a) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921.
24. (b) Reetz, M. T.; Moulin, D.; Gosberg, A, Org. Lett. 2001, 3, 4083.
25. (c) Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311.
26. (d) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932.
27. Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
28. Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 2, Chapter 1.7.
29. For an example of the reaction of chiral boron enolates, see: Ward, D. E.; Lu, W.-L. J. Am. Chem. Soc. 1998, 120, 1098.
30. Hayashi, T.; Tokunaga, N.; Yoshida, K.; Han, J. W. J. Am. Chem. Soc. 2002, 124, 12102.
31. Kramer, G. W.; Brown, H. C. J. Organomet. Chem. 1974, 73, 1.
32. Uson, R.; Oro, L. A.; Cabeza, J. A. Inorg. Synth. 1985, 23, 126.
33. (a) Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
34. (b) Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1989, 67, 20.
35. (c) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
36. (d) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
37. Cramer, R. Inorg. Synth. 1974, 15, 16.