AgOAc-catalyzed aldehyde allylation using allyldimethyl(2-pyridyl)silane

Chemistry Letters

Volumn , Issue 11, 2002, Pages 1084-1085

  Itami, Kenichiro ^a   Kamei, Toshiyuki ^a   Mineno, Masahiro ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLDIMETHYL(2 PYRIDYL)SILANE; SILANE DERIVATIVE; SILVER DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL INTERACTION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 0037027696     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.1084     Document Type: Article

References (41)

1. H. Sakurai, Pure Appl. Chem., 54, 1 (1982); A. Hosomi, Acc. Chem. Res., 21, 200 (1988); I. Fleming, J. Dunoguès, and R. Smithers, Org. React., 37, 57 (1989).
2. H. Sakurai, Pure Appl. Chem., 54, 1 (1982); A. Hosomi, Acc. Chem. Res., 21, 200 (1988); I. Fleming, J. Dunoguès, and R. Smithers, Org. React., 37, 57 (1989).
3. H. Sakurai, Pure Appl. Chem., 54, 1 (1982); A. Hosomi, Acc. Chem. Res., 21, 200 (1988); I. Fleming, J. Dunoguès, and R. Smithers, Org. React., 37, 57 (1989).
4. A. Hosomi and H. Sakurai, Tetrahedron Lett., 1976, 1295.
5. H. Sakurai, Synlett, 1989, 1; C. Chuit, R. J. P. Corriu, C. Reye, and J. C. Young, Chem. Rev., 93, 1371 (1993).
6. H. Sakurai, Synlett, 1989, 1; C. Chuit, R. J. P. Corriu, C. Reye, and J. C. Young, Chem. Rev., 93, 1371 (1993).
7. A. Hosomi, A. Shirahata, and H. Sakurai, Tetrahedron Lett., 1978, 3043.
8. 2Ph: T. Hiyama, M. Obayashi, and M. Sawahata, Tetrahedron Lett., 24, 4113 (1983).
9. 3: R. J. P. Corriu, V. Huynh, and J. J. E. Moreau, J. Organomet. Chem., 259, 283 (1983).
10. Pentacoordinate allylsilicate: G. Cerveau, C. Chuit, R. J. P. Corriu, and C. Reye, J. Organomet. Chem., 328, C17 (1987); M. Kira, K. Sato, and H. Sakurai, J. Am. Chem. Soc., 110, 4599 (1988); A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga, J. Org. Chem., 55, 2415 (1990).
11. Pentacoordinate allylsilicate: G. Cerveau, C. Chuit, R. J. P. Corriu, and C. Reye, J. Organomet. Chem., 328, C17 (1987); M. Kira, K. Sato, and H. Sakurai, J. Am. Chem. Soc., 110, 4599 (1988); A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga, J. Org. Chem., 55, 2415 (1990).
12. Pentacoordinate allylsilicate: G. Cerveau, C. Chuit, R. J. P. Corriu, and C. Reye, J. Organomet. Chem., 328, C17 (1987); M. Kira, K. Sato, and H. Sakurai, J. Am. Chem. Soc., 110, 4599 (1988); A. Hosomi, S. Kohra, K. Ogata, T. Yanagi, and Y. Tominaga, J. Org. Chem., 55, 2415 (1990).
13. 3: S. Kobayashi and K. Nishio, J. Org. Chem., 59, 6620 (1994).
14. 3: I. Chataigner, U. Piarulli, and C. Gennari, Tetrahedron Lett., 40, 3633 (1999).
15. 3: K. Iseki, S. Mizuno, Y. Kuroki, and Y. Kobayashi, Tetrahedron, 55, 977 (1999).
16. 3: S. E. Denmark, D. M. Coe, N. E. Pratt, and B. D. Griedel, J. Org. Chem., 59, 6161 (1994); K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, and Y. Kobayashi, Tetrahedron, 53, 3513 (1997); J. Hellwig, T. Belser, and J. F. K. Müller, Tetrahedron Lett., 42, 5417 (2001); S. E. Denmark and J. Fu, J. Am. Chem. Soc., 123, 9488 (2001).
17. 3: S. E. Denmark, D. M. Coe, N. E. Pratt, and B. D. Griedel, J. Org. Chem., 59, 6161 (1994); K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, and Y. Kobayashi, Tetrahedron, 53, 3513 (1997); J. Hellwig, T. Belser, and J. F. K. Müller, Tetrahedron Lett., 42, 5417 (2001); S. E. Denmark and J. Fu, J. Am. Chem. Soc., 123, 9488 (2001).
18. 3: S. E. Denmark, D. M. Coe, N. E. Pratt, and B. D. Griedel, J. Org. Chem., 59, 6161 (1994); K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, and Y. Kobayashi, Tetrahedron, 53, 3513 (1997); J. Hellwig, T. Belser, and J. F. K. Müller, Tetrahedron Lett., 42, 5417 (2001); S. E. Denmark and J. Fu, J. Am. Chem. Soc., 123, 9488 (2001).
19. 3: S. E. Denmark, D. M. Coe, N. E. Pratt, and B. D. Griedel, J. Org. Chem., 59, 6161 (1994); K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, and Y. Kobayashi, Tetrahedron, 53, 3513 (1997); J. Hellwig, T. Belser, and J. F. K. Müller, Tetrahedron Lett., 42, 5417 (2001); S. E. Denmark and J. Fu, J. Am. Chem. Soc., 123, 9488 (2001).
20. 3: R. M. Angell, A. G. M. Barrett, D. C. Braddock, S. Swallow, and B. D. Vickery, Chem. Commun., 1997, 919.
21. 3: M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto, J. Am. Chem. Soc., 120, 6419 (1998); A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, and P. Kočovský, Org. Lett., 4, 1047 (2002); T. Shimada, A. Kina, S. Ikeda, and T. Hayashi, Org. Lett., 4, 2799 (2002).
22. 3: M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto, J. Am. Chem. Soc., 120, 6419 (1998); A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, and P. Kočovský, Org. Lett., 4, 1047 (2002); T. Shimada, A. Kina, S. Ikeda, and T. Hayashi, Org. Lett., 4, 2799 (2002).
23. 3: M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto, J. Am. Chem. Soc., 120, 6419 (1998); A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, and P. Kočovský, Org. Lett., 4, 1047 (2002); T. Shimada, A. Kina, S. Ikeda, and T. Hayashi, Org. Lett., 4, 2799 (2002).
24. Very recently Shibasaki has developed an efficient catalytic allylation using allyltrimethoxysilane. S. Yamasaki, K. Fujii, R. Wada, M. Kanai, and M. Shibasaki, J. Am. Chem. Soc., 124, 6536 (2002).
25. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 122, 12013 (2000); K. Itami, K. Mitsudo, and J. Yoshida, Angew. Chem., Int. Ed., 40, 2337 (2001); K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Koike, and J. Yoshida, J. Am. Chem. Soc., 123, 6957 (2001); K. Itami, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 8773 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); K. Itami, K. Mitsudo, T. Nokami, T. Kamei, T. Koike, and J. Yoshida, J. Organomet. Chem., 653, 105 (2002).
26. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 122, 12013 (2000); K. Itami, K. Mitsudo, and J. Yoshida, Angew. Chem., Int. Ed., 40, 2337 (2001); K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Koike, and J. Yoshida, J. Am. Chem. Soc., 123, 6957 (2001); K. Itami, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 8773 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); K. Itami, K. Mitsudo, T. Nokami, T. Kamei, T. Koike, and J. Yoshida, J. Organomet. Chem., 653, 105 (2002).
27. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 122, 12013 (2000); K. Itami, K. Mitsudo, and J. Yoshida, Angew. Chem., Int. Ed., 40, 2337 (2001); K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Koike, and J. Yoshida, J. Am. Chem. Soc., 123, 6957 (2001); K. Itami, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 8773 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); K. Itami, K. Mitsudo, T. Nokami, T. Kamei, T. Koike, and J. Yoshida, J. Organomet. Chem., 653, 105 (2002).
28. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 122, 12013 (2000); K. Itami, K. Mitsudo, and J. Yoshida, Angew. Chem., Int. Ed., 40, 2337 (2001); K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Koike, and J. Yoshida, J. Am. Chem. Soc., 123, 6957 (2001); K. Itami, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 8773 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); K. Itami, K. Mitsudo, T. Nokami, T. Kamei, T. Koike, and J. Yoshida, J. Organomet. Chem., 653, 105 (2002).
29. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 122, 12013 (2000); K. Itami, K. Mitsudo, and J. Yoshida, Angew. Chem., Int. Ed., 40, 2337 (2001); K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Koike, and J. Yoshida, J. Am. Chem. Soc., 123, 6957 (2001); K. Itami, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 8773 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); K. Itami, K. Mitsudo, T. Nokami, T. Kamei, T. Koike, and J. Yoshida, J. Organomet. Chem., 653, 105 (2002).
30. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 122, 12013 (2000); K. Itami, K. Mitsudo, and J. Yoshida, Angew. Chem., Int. Ed., 40, 2337 (2001); K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Koike, and J. Yoshida, J. Am. Chem. Soc., 123, 6957 (2001); K. Itami, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 8773 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); K. Itami, K. Mitsudo, T. Nokami, T. Kamei, T. Koike, and J. Yoshida, J. Organomet. Chem., 653, 105 (2002).
31. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 122, 12013 (2000); K. Itami, K. Mitsudo, and J. Yoshida, Angew. Chem., Int. Ed., 40, 2337 (2001); K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Koike, and J. Yoshida, J. Am. Chem. Soc., 123, 6957 (2001); K. Itami, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 8773 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); K. Itami, K. Mitsudo, T. Nokami, T. Kamei, T. Koike, and J. Yoshida, J. Organomet. Chem., 653, 105 (2002).
32. Lewis acid methodology may not be efficient for allyl(2-pyridyl)silane because pyridyl-to-metal coordination could compete with carbonyl activation. In such circumstance, excess Lewis acid may be required. K. Itami, T. Nokami, and J. Yoshida, Adv. Synth. Catal., 344, 441 (2002).
33. Yamamoto has reported that p-Tol-BINAP·AgF complex is a good chiral catalyst for aldehyde allylation using allyltrimethoxysilanes. A. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y. Matsumoto, and H. Yamamoto, Angew. Chem., Int. Ed., 38, 3701 (1999).
34. 3. J. D. Short, S. Attenoux, and D. J. Berrisford, Tetrahedron Lett., 38, 2351 (1997).
35. Zn/AgOAc-promoted aldehyde allylation: T. Ishihara, S. Miwatashi, M. Kuroboshi, and K. Utimoto, Tetrahedron Lett., 32, 1069 (1991); AgOAc-promoted ring enlargement of silacyclobutane: K. Matsumoto, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 32, 6383 (1991).
36. Zn/AgOAc-promoted aldehyde allylation: T. Ishihara, S. Miwatashi, M. Kuroboshi, and K. Utimoto, Tetrahedron Lett., 32, 1069 (1991); AgOAc-promoted ring enlargement of silacyclobutane: K. Matsumoto, K. Miura, K. Oshima, and K. Utimoto, Tetrahedron Lett., 32, 6383 (1991).
37. 3CN (4 mL) was added to the reaction mixture. Extractive work-up and subsequent silica gel chromatography afforded 1-phenyl-3-buten-1-ol (3) (0.85 mmol, 85%).
38. N. Asao, A. Shibato, Y. Itagaki, F. Jourda, and K. Maruoka, Tetrahedron Lett., 39, 3177 (1998); Z. Wang, P. Kisanga, and J. G. Verkade, J. Org. Chem., 64, 6459 (1999).
39. N. Asao, A. Shibato, Y. Itagaki, F. Jourda, and K. Maruoka, Tetrahedron Lett., 39, 3177 (1998); Z. Wang, P. Kisanga, and J. G. Verkade, J. Org. Chem., 64, 6459 (1999).
40. J. Yoshida, K. Itami, K. Mitsudo, and S. Suga, Tetrahedron Lett., 40, 3403 (1999); J. Yoshida and K. Itami, Yuki Gosei Kagaku Kyokaishi, 59, 1086 (2001).
41. J. Yoshida, K. Itami, K. Mitsudo, and S. Suga, Tetrahedron Lett., 40, 3403 (1999); J. Yoshida and K. Itami, Yuki Gosei Kagaku Kyokaishi, 59, 1086 (2001).