Stereoselective synthesis of 3-alkylideneoxindoles by rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryland alkenylboronic acids

Organic Letters

Volumn 9, Issue 24, 2007, Pages 5075-5077

  Miura, Tomoya ^a   Takahashi, Yusuke ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; INDOLE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

BORONIC ACIDS; CATALYSIS; CYCLIZATION; INDOLES; ISOCYANATES; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 36849061632     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7024185     Document Type: Article

References (36)

1. For reviews, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
2. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
3. Miura, T.; Murakami, M. Chem. Commun. 2007, 217.
4. For selected examples, see: (a) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
5. (b) Shintani, R.; Tsurusaki, A.; Okamoto, K.; Hayashi, T. Angew. Chem., Int. Ed. 2005, 44, 3909.
6. (c) Tseng, N.-W.; Mancuso, J.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 5338.
7. (d) Harada, Y.; Nakanishi, J.; Fujihara, H.; Tobisu, M.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2007, 129, 5766 and references therein.
8. (a) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918.
9. (b) Murakami, M.; Igawa, H. Helv. Chim. Acta 2002, 85, 4182.
10. (c) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123.
11. (d) Genin, E.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2004, 45, 4157.
12. (a) Koike, T.; Takahashi, M.; Arai, N.; Mori, A. Chem. Lett. 2004, 33, 1364.
13. (b) Miura, T.; Takahashi, Y.; Murakami, M. Chem. Commun. 2007, 3577.
14. Kamijo, S.; Sasaki, Y.; Kanazawa, C.; Schüβeler, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 7718.
15. For recent examples of the synthesis of 3-alkylideneoxindoles with catalysis of transition metals, see: (a) Fielding, M. R.; Grigg, R.; Urch, C. J. Chem. Commum. 2000, 2239.
16. (b) Yanada, R.; Obika, S.; Oyama, M.; Takemoto, Y. Org. Lett. 2004, 6, 2825.
17. (c) D'Souza, D. M.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 153.
18. (d) Cheung, W. S.; Patch, R. J.; Player, M. R. J. Org. Chem. 2005, 70, 3741.
19. (e) Yanada, R.; Obika, S.; Inokuma, T.; Yanada, K.; Yamashita, M.; Ohta, S.; Takemoto, Y. J. Org. Chem. 2005, 70, 6972.
20. (f) Kobayashi, Y.; Kamisaki, H.; Yanada, K.; Yanada, R.; Takemoto, Y. Tetrahedron Lett. 2005, 46, 7549.
21. (g) Shintani, R.; Yamagami, T.; Hayashi, T. Org. Lett. 2006, 8, 4799.
22. (h) Pinto, A.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 3291.
23. For the intermediates in total synthesis, see: (a) Carroll, W. A.; Grieco, P. A. J. Am. Chem. Soc. 1993, 115, 1164.
24. (b) Rasmussen, H. B.; MacLeod, J. K. J. Nat. Prod. 1997, 60, 1152.
25. (c) Lin, S.; Yang, Z.-Q.; Kwok, B. H. B.; Koldoskiy, M.; Crews, C. M.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6347.
26. (d) Trost, B. M.; Cramer, N.; Bernsmann, H. J. Am. Chem. Soc. 2007, 129, 3086.
27. (a) Sun, L.; Tran, N.; Tang, F.; App, H.; Hirth, P.; McMahon, G.; Tang, C. J. Med. Chem. 1998, 41, 2588.
28. (b) Vieth, M.; Cummins, D. J. J. Med. Chem. 2000, 43, 3020.
29. (c) Woodard, C. L.; Li, Z.; Kathcart, A. K.; Terrell, J.; Gerena, L.; Lopez-Sanchez, M.; Kyle, D. E.; Bhattacharjee, A. K.; Nichols, D. A.; Ellis, W.; Prigge, S. T.; Geyer, J. A.; Waters, N. C. J. Med. Chem. 2003, 46, 3877.
30. (d) Pandit, B.; Sun, Y.; Chen, P.; Sackett, D. L.; Hu, Z.; Rich, W.; Li, C.; Lewis, A.; Schaefer, K.; Li, P.-K. Bioorg. Med. Chem. 2006, 14, 6492.
31. (e) Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Kunkel, M. W. J. Med. Chem. 2006, 49, 6922.
32. For 1,1-carborhodation of terminal alkynes with organoboron reagents through a rhodium vinylidene intermediate, see: Chen, Y.; Lee, C. J. Am. Chem. Soc. 2006, 128, 15598.
33. Zhao, P.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 1876.
34. Kurahashi, T.; Shinokuba, H.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 6336.
35. For intermolecular oxidative cyclization with the CC triple bond of an alkyne and the N=C double bond of an isocyanate, see: Yu, R. T.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 12370.
36. 1H NMR.