Rhodium-catalyzed addition/ring-opening reaction of arylboronic acids with cyclobutanones

Organic Letters

Volumn 6, Issue 8, 2004, Pages 1257-1259

  Matsuda, Takanori ^a   Makino, Masaomi ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; CYCLOBUTANONE DERIVATIVE; RHODIUM COMPLEX;

ADDITION REACTION; ARTICLE; CATALYSIS; METHODOLOGY; REACTION ANALYSIS; RING OPENING;

EID: 2542504377     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049833a     Document Type: Article

References (35)

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10. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
11. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
12. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
13. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (1) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
14. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
15. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
16. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
17. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
18. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
19. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
20. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
21. For reactions with α,β-unsaturated carbonyl compounds, see: (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110. (c) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000. For reactions with aldehydes and ketones, see: (d) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. (e) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450. (f) Takezawa, A.; Yamaguchi, K.; Ohmura, T.; Yamamoto, Y.; Miyaura, N. Synlett 2002, 1733. For reactions with alkenes, see: (g) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464. (h) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (i) Murakami, M.; Igawa, H. Chem. Commun. 2002, 390. For reaction with alkynes, see: (j) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918. (k) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 55, 4182. (l) Lautens, M.; Yoshida, M. J. Org. Chem. 2003, 68, 762.
22. For reviews: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
23. For reviews: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
24. 3 ≈ none.
25. 3 showed little accelerating effect for the reaction with less sterically hindered phenylboronic acid.
26. Tertiary cyclobutanol 4aa was synthesized independently by the reaction of 1a with the Grignard reagent as a diastereomeric mixture (cis: trans = 74:26).
27. 1H NMR; however, the relative stereochemistries were not determined.
28. For β-carbon elimination from Pd(II) cyclobutanolate, see: (a) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010. (b) Nishimura, T.; Ohe, K.; Uemura, S. J. Org. Chem. 2001, 66, 1455. (c) Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862.
29. For β-carbon elimination from Pd(II) cyclobutanolate, see: (a) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010. (b) Nishimura, T.; Ohe, K.; Uemura, S. J. Org. Chem. 2001, 66, 1455. (c) Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862.
30. For β-carbon elimination from Pd(II) cyclobutanolate, see: (a) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010. (b) Nishimura, T.; Ohe, K.; Uemura, S. J. Org. Chem. 2001, 66, 1455. (c) Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862.
31. For transition metal-hydride elimination followed by re-addition with opposite regiochemistry, see: (a) Yoshida, K.; Hayashi, T. J. Am. Chem. Soc. 2003, 125, 2872. (b) Gagnier, S. V.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 4804. (c) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (d) Ittel, S. D.; Johnson, L. K. Chem. Rev. 2000, 100, 1169.
32. For transition metal-hydride elimination followed by re-addition with opposite regiochemistry, see: (a) Yoshida, K.; Hayashi, T. J. Am. Chem. Soc. 2003, 125, 2872. (b) Gagnier, S. V.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 4804. (c) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (d) Ittel, S. D.; Johnson, L. K. Chem. Rev. 2000, 100, 1169.
33. For transition metal-hydride elimination followed by re-addition with opposite regiochemistry, see: (a) Yoshida, K.; Hayashi, T. J. Am. Chem. Soc. 2003, 125, 2872. (b) Gagnier, S. V.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 4804. (c) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (d) Ittel, S. D.; Johnson, L. K. Chem. Rev. 2000, 100, 1169.
34. For transition metal-hydride elimination followed by re-addition with opposite regiochemistry, see: (a) Yoshida, K.; Hayashi, T. J. Am. Chem. Soc. 2003, 125, 2872. (b) Gagnier, S. V.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 4804. (c) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (d) Ittel, S. D.; Johnson, L. K. Chem. Rev. 2000, 100, 1169.
35. For synthetic applications of cyclobutane derivatives, see: Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485.