Acceleration effect of Lewis acid in allylboration of aldehydes: Catalytic, regiospecific, diastereospecific, and enantioselective synthesis of homoallyl alcohols

Journal of the American Chemical Society

Volumn 124, Issue 42, 2002, Pages 12414-12415

  Ishiyama, Tatsuo ^a   Ahiko, Taka Aki ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037164048     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0210345     Document Type: Article

References (26)

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7. For diastereospecific allylsilation, see: (a) Hosomi, A.; Kohara, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987. 1517. (b) Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328. C17. (c) Kira, M.; Kobayashi, M.; Sakurai, H. J. Am. Chem. Soc. 1988, 110. 4599. For diastereospecific allylstannation, see: (d) Servens, C.; Pereyre, M. J. Organomet. Chem. 1972, 35, C20. (e) Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489.
8. For diastereospecific allylsilation, see: (a) Hosomi, A.; Kohara, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987. 1517. (b) Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328. C17. (c) Kira, M.; Kobayashi, M.; Sakurai, H. J. Am. Chem. Soc. 1988, 110. 4599. For diastereospecific allylstannation, see: (d) Servens, C.; Pereyre, M. J. Organomet. Chem. 1972, 35, C20. (e) Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489.
9. For diastereospecific allylsilation, see: (a) Hosomi, A.; Kohara, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987. 1517. (b) Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328. C17. (c) Kira, M.; Kobayashi, M.; Sakurai, H. J. Am. Chem. Soc. 1988, 110. 4599. For diastereospecific allylstannation, see: (d) Servens, C.; Pereyre, M. J. Organomet. Chem. 1972, 35, C20. (e) Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489.
10. For diastereospecific allylsilation, see: (a) Hosomi, A.; Kohara, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987. 1517. (b) Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328. C17. (c) Kira, M.; Kobayashi, M.; Sakurai, H. J. Am. Chem. Soc. 1988, 110. 4599. For diastereospecific allylstannation, see: (d) Servens, C.; Pereyre, M. J. Organomet. Chem. 1972, 35, C20. (e) Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489.
11. For diastereospecific allylsilation, see: (a) Hosomi, A.; Kohara, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1987. 1517. (b) Cerveau, G.; Chuit, C.; Corriu, R. J. P.; Reye, C. J. Organomet. Chem. 1987, 328. C17. (c) Kira, M.; Kobayashi, M.; Sakurai, H. J. Am. Chem. Soc. 1988, 110. 4599. For diastereospecific allylstannation, see: (d) Servens, C.; Pereyre, M. J. Organomet. Chem. 1972, 35, C20. (e) Yamamoto, Y.; Maruyama, K.; Matsumoto, K. J. Chem. Soc., Chem. Commun. 1983, 489.
12. (a) Cozzi, P. G.; Tagliavini. E.; Umani-Ronchi, A. Gazz, Chim. Ital. 1997, 124, 247.
13. (b) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998. 75, 12.
14. (c) Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527.
15. (d) Yanagisawa, A. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, p 965.
16. For chiral Lewis base/allylic trichlorosilane approaches, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (c) Iseki. K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (d) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 and references cited therein.
17. For chiral Lewis base/allylic trichlorosilane approaches, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (c) Iseki. K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (d) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 and references cited therein.
18. For chiral Lewis base/allylic trichlorosilane approaches, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (c) Iseki. K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (d) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 and references cited therein.
19. For chiral Lewis base/allylic trichlorosilane approaches, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419. (c) Iseki. K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron 1999, 55, 977. (d) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488 and references cited therein.
20. (a) The related allyltrifluoroborate salts add to aldehydes using a strong Lewis acid catalyst, while it is not a formal mode of Lewis acid activation: Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A. J. Synthesis 2000, 990. (b) Hoffmann and co-workers have reported intramolecular allylboration of acetals, in which they have employed a Lewis acid to hydrolyze the acetal moiety to aldehyde. Although they have not discussed effects of the Lewis acids in the allylboration, the reactions may be accelerated by them: Hoffmann, R. W.; Krüger, J.; Brückner, D. New J. Chem. 2001, 25, 102 and references cited therein.
21. (a) The related allyltrifluoroborate salts add to aldehydes using a strong Lewis acid catalyst, while it is not a formal mode of Lewis acid activation: Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A. J. Synthesis 2000, 990. (b) Hoffmann and co-workers have reported intramolecular allylboration of acetals, in which they have employed a Lewis acid to hydrolyze the acetal moiety to aldehyde. Although they have not discussed effects of the Lewis acids in the allylboration, the reactions may be accelerated by them: Hoffmann, R. W.; Krüger, J.; Brückner, D. New J. Chem. 2001, 25, 102 and references cited therein.
22. Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.; Park, J. C. J. Org. Chem. 1990, 55, 4109.
23. For a review, see: Kobayashi, S. Synlett 1994, 689.
24. The addition of 2a (1.1 mmol) to benzaldehyde (1.0 mmol) in the presence of HCI (0.1 mmol) in toluene/ether solvent (6 mL) at - 78°C for 16 h resulted in a 21% yield of the corresponding homoallyl alcohol.
25. Gothelf, A. S.; Hansen, T.; Jorgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 854.
26. Kobayashi, S.; Araki, M.; Hachiya, I. J. Org. Chem. 1994, 59, 3758.