Rhodium-catalyzed enantioselective [2 + 2 + 2] cycloaddition of tosylamide-linked 5-allenal and 5-allenone with internal alkynes

Chemistry Letters

Volumn 43, Issue 8, 2014, Pages 1260-1262

  Sakashita, Kazuki ^b   Masutomi, Koji ^b   Noguchi, Keiichi ^b   Tanaka, Ken ^a,b,c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906487821     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.140448     Document Type: Article

References (36)

1. a) G. Domínguez, J. Pérez-Castells, Chem. Soc. Rev. 2011, 40, 3430.
2. b) N. Agenet, O. Buisine, F. Slowinski, V. Gandon, C. Aubert, M. Malacria, in Organic Reactions, ed. by L. E. Overman, John Wiley & Sons, Hoboken, 2007, Vol. 68, p. 1. doi:10.1002/0471264180.or068.01.
3. c) P. R. Chopade, J. Louie, Adv. Synth. Catal. 2006, 348, 2307.
4. T. Tsuda, T. Kiyoi, T. Miyane, T. Saegusa, J. Am. Chem. Soc. 1988, 11 0, 8570.
5. Y. Yamamoto, H. Takagishi, K. Itoh, J. Am. Chem. Soc. 2002, 124, 6844.
6. a) T. N. Tekevac, J. Louie, Org. Lett. 2005, 7, 4037.
7. b) T. N. Tekavec, J. Louie, J. Org. Chem. 2008, 73, 2641.
8. B. Bennacer, M. Fujiwara, S.-Y. Lee, I. Ojima, J. Am. Chem. Soc. 2005, 127, 17756.
9. J. R. Kong, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 16040.
10. a) K. Tanaka, Y. Otake, A. Wada, K. Noguchi, M. Hirano, Org. Lett. 2007, 9, 2203.
11. b) K. Tsuchikama, Y. Yoshinami, T. Shibata, Synlett 1395.
12. c) K. Tanaka, R. Tanaka, G. Nishida, M. Hirano, Synlett 2017.
13. d) K. Tanaka, Y. Otake, H. Sagae, K. Noguchi, M. Hirano, Angew. Chem., Int. Ed. 2008, 47, 1312.
14. e) Y. Otake, R. Tanaka, K. Tanaka, Eur. J. Org. Chem. 2009, 2737.
15. f) T. Suda, K. Noguchi, K. Tanaka, Angew. Chem., Int. Ed. 2011, 50, 4475.
16. g) Y. Miyauchi, M. Kobayashi, K. Tanaka, Angew. Chem., Int. Ed. 2011, 50, 10922.
17. h) Y. Miyauchi, K. Noguchi, K. Tanaka, Org. Lett. 2012, 14, 5856.
18. i) M. Ishida, Y. Shibata, K. Noguchi, K. Tanaka, Chem. Eur. J. 2011, 17, 12578.
19. a) D. F. Harvey, B. M. Johnson, C. S. Ung, K. P. C. Vollhardt, Synlett 1989, 15.
20. b) R. Gleiter, V. Schehlmann, Tetrahedron Lett. 1989, 30, 2893.
21. c) T. Takahashi, Y. Li, T. Ito, F. Xu, K. Nakajima, Y. Liu, J. Am. Chem. Soc. 2002, 124, 1144.
22. Y. Oonishi, Y. K itano, Y. Sato, Tetrahedron 2013, 69, 7713.
23. a) N. N. Noucti, E. J. Alexanian, Angew. Chem., Int. Ed. 2013, 52, 8424.
24. b) A. T. Brusoe, R. V. Edwankar, E. J. Alexanian, Org. Lett. 2012, 14, 6096.
25. c) N. Saito, T. Ichimaru, Y. Sato, Chem. Asian J. 2012, 7, 1521.
26. d) T. Miura, M. Morimoto, M. Murakami, J. Am. Chem. Soc. 2010, 132, 15836.
27. e) X. Jiang, S. Ma, J. Am. Chem. Soc. 2007, 129, 11600.
28. f) M. Petit, C. Aubert, M. Malacria, Tetrahedron 2006, 62, 10582.
29. g) S. Ma, P. Lu, L. Lu, H. Hou, J. Wei, Q. He, Z. Gu, X. Jiang, X. Jin, Angew. Chem., Int. Ed. 2005, 44, 5275.
30. h) J.-C. Hsieh, D. K. Rayabarapu, C.-H. Cheng, Chem. Commun. 2004, 532.
31. i) M.-S. Wu, M. Shanmugasundaram, C.-H. Cheng, Chem. Commun. 2003, 718.
32. j) M. Shanmugasundaram, M.-S. Wu, M. Jeganmohan, C.-W. Huang, C.-H. Cheng, J. Org. Chem. 2002, 67, 7724.
33. a) R. Tanaka, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2010, 132, 1238.
34. b) K. Masuda, N. Sakiyama, R. Tanaka, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2011, 133, 6918.
35. c) Y. Tajima, M. Kobayashi, K. Noguchi, K. Tanaka, Eur. J. Org. Chem. 2013, 5266.
36. Y. Oonishi, A. Hosotani, Y. Sato, Angew. Chem., Int. Ed. 2012, 51, 11548.