A novel axially chiral 2,2′-bipyridine N,N′-dioxide. Its preparation and use for asymmetric allylation of aldehydes with allyl(trichloro)silane as a highly efficient catalyst

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2799-2801

  Shimada, Toyoshi ^a   Kina, Asato ^a   Ikeda, Syushiro ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000761076     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026376u     Document Type: Article

References (31)

1. (a) Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328, C17.
2. (b) Hosomi, A.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987, 1517.
3. (c) Kira, M.; Sato, K.; Sakurai, H. J. Am. Chem. Soc. 1988, 110, 4599.
4. Hayashi, T.; Matsumoto, Y.; Kiyoi, T.; Ito, Y.; Kohra, S.; Tominaga, Y.; Hosomi, A. Tetrahedron Lett. 1988, 29, 5667.
5. (a) Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1993, 34, 3453.
6. (b) Kobayashi, S.; Nishio, K. Synthesis 1994, 457.
7. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161.
8. For a review on catalytic asymmetric allylation: Yanagisawa, A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Germany, 1999; Chapter 27.
9. (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021.
10. (b) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488
11. (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149.
12. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 3513.
13. (c) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767.
14. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977.
15. (a) Nakajima, M.; Sasaki, Y.; Shiro, M.; Hashimoto, S. Tetrahedron: Asymmetry 1997, 8, 341.
16. (b) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419.
17. (a) Angell, R. M.; Barrett, A. G. M.; Braddock, D. C.; Swallow, S.; Vickery, B. D. Chem. Commun. 1997, 919.
18. (b) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633.
19. (c) Hellwig, J.; Belser, T.; Müller, J. F. K. Tetrahedron Lett. 2001, 42, 5417.
20. For books containing Lewis acid-catalyzed asymmetric reactions: (a) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000.
21. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, Germany, 1999.
22. (c) Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley: New York, 2001.
23. Very recently, new chiral bipyridine N,N′-dioxides have been prepared and used for Lewis base-catalyzed asymmetric addition to carbonyl compounds: (a) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047.
24. (b) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
25. Dietrich-Buchecker, C. O.; Marnot, P. A.; Sauvage, J. P. Tetrahedron Lett. 1982, 23, 5291.
26. The diester formation reaction at a low temperature gave the other diastereoisomer as a kinetic product with high selectivity (over 95% selectivity), which is isomerized into the thermodynamic isomer by heating. These phenomena will be described in detail elsewhere.
27. The absolute configuration was determined by X-ray structure analysis of the cyclic diester 5a (see Supporting Information).
28. The allylation with 0.1 mol % of (R)-2a at -45°C did not proceed in toluene, diethyl ether, or THF.
29. A few examples of this level of low catalyst loading have been reported in the Lewis acid-catalyzed Hetero-Diels-Alder reactions: (a) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599, where 0.05 mol % of catalyst was used.
30. (b) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366, where 0.01 mol % of catalyst was used.
31. (c) Long, J.; Hu, J.; Shen, X.; Ji, B.; Ding, K. J. Am. Chem. Soc. 2002, 124, 10, where 0.005 mol % of catalyst was used.