Novel alkenylative cyclization using a ruthenium catalyst

Journal of the American Chemical Society

Volumn 125, Issue 19, 2003, Pages 5606-5607

  Mori, Miwako ^a   Saito, Nozomi ^a   Tanaka, Daisuke ^a   Takimoto, Masanori ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKENYL GROUP; ARGON; CARBENE; ETHYLENE; ETHYLENE DERIVATIVE; IMIDAZOLE DERIVATIVE; RUTHENACYCLOPENTENE; RUTHENIUM; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENZYME SUBSTRATE; OXIDATION; ROOM TEMPERATURE;

EID: 0038296931     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029747a     Document Type: Article

References (37)

1. For recent review on metathesis, see: (a) Fürsmer, A. Topics in Organometallic Chemistry; Springer-Verlag: Berlin, Heidelberg, 1998; Vol. 1. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
2. For recent review on metathesis, see: (a) Fürsmer, A. Topics in Organometallic Chemistry; Springer-Verlag: Berlin, Heidelberg, 1998; Vol. 1. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
3. For recent review on metathesis, see: (a) Fürsmer, A. Topics in Organometallic Chemistry; Springer-Verlag: Berlin, Heidelberg, 1998; Vol. 1. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
4. For recent review on metathesis, see: (a) Fürsmer, A. Topics in Organometallic Chemistry; Springer-Verlag: Berlin, Heidelberg, 1998; Vol. 1. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
5. For recent review on metathesis, see: (a) Fürsmer, A. Topics in Organometallic Chemistry; Springer-Verlag: Berlin, Heidelberg, 1998; Vol. 1. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
6. For recent review on metathesis, see: (a) Fürsmer, A. Topics in Organometallic Chemistry; Springer-Verlag: Berlin, Heidelberg, 1998; Vol. 1. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (d) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75. (e) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
7. (a) Weskamp, A. T.; Schattenmann, W. C.; Spiegler, M.; Hemmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490.
8. (b) Huang, J.; Stevens, E. D.; Nolan, S. P.; Peterson, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
9. (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247.
10. (d) Jafarpour, L.; Nolan, S. P. Organometallics 2000, 19, 2055.
11. (e) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
12. (a) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
13. (b) Choi, T.-L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277.
14. (c) Grela, K.; Bieniek, M. Tetrahedron Lett. 2001, 42, 6425.
15. (d) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751.
16. (e) Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
17. (f) Pietraszuk, C.; Marciniec, B.; Fischer, H. Organometallics 2000, 19, 913.
18. Review on enyne metathesis, see: Mori, M. Top. Organomet. Chem. 1998, 1, 133.
19. (a) Kitamura, T.; Sato, Y.; Mori, M. Chem. Commun. 2001, 1258.
20. (b) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678.
21. (a) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
22. (b) Kinoshita, A.; Mori, M. Synlett 1994, 1020.
23. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
24. Review for recent ruthenium-catalyzed reaction: (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2002, 124, 5025. (c) Trost, B. M.; Chisholm, J. D.; Wrobleski, S. T.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420.
25. Review for recent ruthenium-catalyzed reaction: (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2002, 124, 5025. (c) Trost, B. M.; Chisholm, J. D.; Wrobleski, S. T.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420.
26. Review for recent ruthenium-catalyzed reaction: (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2002, 124, 5025. (c) Trost, B. M.; Chisholm, J. D.; Wrobleski, S. T.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420.
27. Insertion of alkyne: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. Insertion of alkene: (b) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310. (c) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610. (d) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564. Insertion of CO: (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Mural, S. J. Org. Chem. 1997, 62, 3762. [5 + 2] cycloaddition: (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379. (h) Trost, B. M.; Schen, H. C. Org. Lett. 2000, 2, 2523.
28. Insertion of alkyne: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. Insertion of alkene: (b) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310. (c) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610. (d) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564. Insertion of CO: (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Mural, S. J. Org. Chem. 1997, 62, 3762. [5 + 2] cycloaddition: (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379. (h) Trost, B. M.; Schen, H. C. Org. Lett. 2000, 2, 2523.
29. Insertion of alkyne: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. Insertion of alkene: (b) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310. (c) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610. (d) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564. Insertion of CO: (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Mural, S. J. Org. Chem. 1997, 62, 3762. [5 + 2] cycloaddition: (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379. (h) Trost, B. M.; Schen, H. C. Org. Lett. 2000, 2, 2523.
30. Insertion of alkyne: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. Insertion of alkene: (b) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310. (c) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610. (d) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564. Insertion of CO: (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Mural, S. J. Org. Chem. 1997, 62, 3762. [5 + 2] cycloaddition: (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379. (h) Trost, B. M.; Schen, H. C. Org. Lett. 2000, 2, 2523.
31. Insertion of alkyne: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. Insertion of alkene: (b) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310. (c) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610. (d) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564. Insertion of CO: (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Mural, S. J. Org. Chem. 1997, 62, 3762. [5 + 2] cycloaddition: (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379. (h) Trost, B. M.; Schen, H. C. Org. Lett. 2000, 2, 2523.
32. Insertion of alkyne: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. Insertion of alkene: (b) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310. (c) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610. (d) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564. Insertion of CO: (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Mural, S. J. Org. Chem. 1997, 62, 3762. [5 + 2] cycloaddition: (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379. (h) Trost, B. M.; Schen, H. C. Org. Lett. 2000, 2, 2523.
33. Insertion of alkyne: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. Insertion of alkene: (b) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310. (c) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610. (d) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564. Insertion of CO: (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Mural, S. J. Org. Chem. 1997, 62, 3762. [5 + 2] cycloaddition: (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379. (h) Trost, B. M.; Schen, H. C. Org. Lett. 2000, 2, 2523.
34. Insertion of alkyne: (a) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. Insertion of alkene: (b) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310. (c) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610. (d) Kondo, T.; Kaneko, Y.; Tsunawaki, F.; Okada, T.; Shiotsuki, M.; Morisaki, Y.; Mitsudo, T. Organometallics 2002, 21, 4564. Insertion of CO: (e) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Mural, S. J. Org. Chem. 1997, 62, 3762. [5 + 2] cycloaddition: (g) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379. (h) Trost, B. M.; Schen, H. C. Org. Lett. 2000, 2, 2523.
35. Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804.
36. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233.
37. Oshima, N.; Suzuki, H.; Moro-oka, Y. Chem. Lett. 1984, 1161.