Highly chemo-, regio-, and enantioselective rhodium-catalyzed cross-cyclotrimerization of two different alkynes with alkenes

Angewandte Chemie - International Edition

Volumn 53, Issue 11, 2014, Pages 2956-2959

  Hara, Jun ^a   Ishida, Mana ^a   Kobayashi, Masayuki ^a   Noguchi, Keiichi ^a   Tanaka, Ken ^a,b  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

alkenes; alkynes; asymmetric catalysis; cyclotrimerization; multicomponent reactions; rhodium

Indexed keywords

ACETYLENEDICARBOXYLATE; ALKYNES; ASYMMETRIC CATALYSIS; CHEMO-SELECTIVITY; CYCLOTRIMERIZATION; ENANTIOSELECTIVE; MULTI-COMPONENT REACTIONS; RHODIUM-CATALYZED;

CATALYSIS; ENANTIOSELECTIVITY; HYDROCARBONS; OLEFINS; RHODIUM; STEEL BEAMS AND GIRDERS;

RHODIUM COMPOUNDS;

EID: 84896754276     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201310336     Document Type: Article

References (54)

1. Transition-Metal-Mediated Aromatic Ring Construction (Ed.:, K. Tanaka,), Wiley, Hoboken, 2013, chap. 1-11
2. S. Okamoto, Y. Sugiyama, Synlett 2013, 1044
3. D. L. J. Broere, E. Ruijter, Synthesis 2012, 2639
4. Y. Shibata, K. Tanaka, Synthesis 2012, 323
5. K. Tanaka, Heterocycles 2012, 85, 1017
6. S. Okamoto, Heterocycles 2012, 85, 1579
7. N. Weding, M. Hapke, Chem. Soc. Rev. 2011, 40, 4525
8. G. Domínguez, J. Pérez-Castells, Chem. Soc. Rev. 2011, 40, 3430
9. P. A. Inglesby, P. A. Evans, Chem. Soc. Rev. 2010, 39, 2791
10. S. Perreault, T. Rovis, Chem. Soc. Rev. 2009, 38, 3149
11. B. R. Galan, T. Rovis, Angew. Chem. 2009, 121, 2870
12. Angew. Chem. Int. Ed. 2009, 48, 2830
13. K. Tanaka, Chem. Asian J. 2009, 4, 508
14. J. A. Varela, C. Saá, Synlett 2008, 2571
15. T. Shibata, K. Tsuchikama, Org. Biomol. Chem. 2008, 6, 1317
16. K. Tanaka, Synlett 2007, 1977
17. B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085.
18. N. Mori, S. Ikeda, K. Odashima, Chem. Commun. 2001, 181
19. Y. Ura, Y. Sato, H. Tsujita, T. Kondo, M. Imachi, T. Mitsudo, J. Mol. Catal. A 2005, 239, 166; For a stoichiometric reaction, see
20. T. Takahashi, Z. Xi, A. Yamazaki, Y. Liu, K. Nakajima, M. Kotora, J. Am. Chem. Soc. 1998, 120, 1672.
21. N. Mori, S. Ikeda, Y. Sato, J. Am. Chem. Soc. 1999, 121, 2722.
22. Y. Satoh, Y. Obora, Org. Lett. 2011, 13, 2568.
23. S. Komagawa, S. Saito, Angew. Chem. 2006, 118, 2506
24. Angew. Chem. Int. Ed. 2006, 45, 2446
25. R. Yamasaki, I. Sotome, S. Koma-gawa, I. Azumaya, H. Masu, S. Saito, Tetrahedron Lett. 2009, 50, 1143
26. S. Komagawa, K. Takeuchi, I. Sotome, I. Azumaya, H. Masu, R. Yamasaki, S. Saito, J. Org. Chem. 2009, 74, 3323
27. R. Yamasaki, N. Terashima, I. Sotome, S. Komagawa, S. Saito, J. Org. Chem. 2010, 75, 480
28. R. Yamasaki, M. Ohashi, K. Maeda, T. Kitamura, M. Nakagawa, K. Kato, T. Fujita, R. Kamura, K. Kinoshita, H. Masu, I. Azumaya, S. Ogoshi, S. Saito, Chem. Eur. J. 2013, 19, 3415.
29. H. Hara, M. Hirano, K. Tanaka, Org. Lett. 2008, 10, 2537
30. H. Hara, M. Hirano, K. Tanaka, Tetrahedron 2009, 65, 5093.
31. M. Kobayashi, T. Suda, K. Noguchi, K. Tanaka, Angew. Chem. 2011, 123, 1702
32. Angew. Chem. Int. Ed. 2011, 50, 1664.
33. S. Ikeda, H. Kondo, T. Arii, K. Odashima, Chem. Commun. 2002, 2422
34. Y. Shibata, K. Noguchi, M. Hirano, K. Tanaka, Org. Lett. 2008, 10, 2825.
35. S. Ogoshi, A. Nishimura, M. Ohashi, Org. Lett. 2010, 12, 3450; For those of two identical alkenes with alkynes, see
36. A. Nishimura, M. Ohashi, S. Ogoshi, J. Am. Chem. Soc. 2012, 134, 15692
37. R. B. Dateer, B. S. Shaibu, R.-S. Liu, Angew. Chem. 2012, 124, 117
38. Angew. Chem. Int. Ed. 2012, 51, 113
39. D. Holte, D. C. G. Götz, P. B. Baran, J. Org. Chem. 2012, 77, 825.
40. Y. Yamamoto, J. Ishii, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 2004, 126, 3712
41. Y. Yamamoto, J. Ishii, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 2005, 127, 9625
42. G. Chouraqui, M. Petit, C. Aubert, M. Malacria, Org. Lett. 2004, 6, 1519
43. B. L. Gray, X. Wang, W. C. Brown, L. Kuai, S. L. Schreiber, Org. Lett. 2008, 10, 2621
44. T. J. Martin, T. Rovis, Angew. Chem. 2013, 125, 5476
45. Angew. Chem. Int. Ed. 2013, 52, 5368.
46. M. Kobayashi, K. Tanaka, Chem. Eur. J. 2012, 18, 9225.
47. T. Sambaiah, L.-P. Li, D.-J. Huang, C.-H. Lin, D. K. Rayabarapu, C.-H. Cheng, J. Org. Chem. 1999, 64, 3663
48. Y. Nakao, H. Idei, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2009, 131, 15996
49. H. Horie, T. Kurahashi, S. Matsubara, Chem. Commun. 2010, 46, 7229
50. CCDC 972328 [(+)- 5 dab ] and CCDC 972329 [(+)- 5 daf ] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
51. K. Tanaka, K. Shirasaka, Org. Lett. 2003, 5, 4697
52. K. Tanaka, K. Toyoda, A. Wada, K. Shirasaka, M. Hirano, Chem. Eur. J. 2005, 11, 1145.
53. K. Masutomi, N. Sakiyama, K. Noguchi, K. Tanaka, Angew. Chem. 2012, 124, 13208
54. Angew. Chem. Int. Ed. 2012, 51, 13031.