Rhodium(II)-Catalyzed Cycloaddition Reactions of Non-classical 1,5-Dipoles for the Formation of Eight-Membered Heterocycles

Angewandte Chemie - International Edition

Volumn 54, Issue 46, 2015, Pages 13715-13718

  Lee, Dong Jin ^a   Ko, Donguk ^a   Yoo, Eun Jeong ^a  

^a Kangwon National University   (South Korea)

Author keywords

cycloaddition; eight membered heterocycles; homogeneous catalysis; rhodium; zwitterions

Indexed keywords

CYCLOADDITION; RHODIUM;

CYCLOADDITION REACTION; HETEROCYCLES; HIGH SELECTIVITY; HIGHER-ORDER; HOMOGENEOUS CATALYSIS; MILD REACTION CONDITIONS; PYRIDINIUM; ZWITTERIONS;

CATALYSIS;

EID: 84946497886     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201506764     Document Type: Article

References (41)

1. X. Xu, M. P. Doyle, Acc. Chem. Res. 2014, 47, 1396;
2. K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863;
3. 1,3-Dipolar Cycloaddition Chemistry, Vol. 1 & 2 (Ed.:, A. Padwa,), Wiley, New York, 1984, p. 1521.
4. R. Huisgen, in Topics in Heterocyclic Chemistry (Ed.:, R. Castle,), Wiley, New York, 1969, chap. 8;
5. A. Padwa, S. R. Harring, M. A. Semones, J. Org. Chem. 1998, 63, 44;
6. I. Ungureanu, P. Klotz, A. Schoenfelder, A. Mann, Chem. Commun. 2001, 958;
7. V. Nair, A. R. Sreekanth, N. Abhilash, M. M. Bhadbhade, R. C. Gonnade, Org. Lett. 2002, 4, 3575;
8. B. Alcaide, P. Almendros, I. Fernández, C. Lázaro-Milla, Chem. Commun. 2015, 51, 3395;
9. Y. Li, X. Su, W. Zhou, W. Li, J. Zhang, Chem. Eur. J. 2015, 21, 4224.
10. X.-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716;
11. R. A. Novikov, A. V. Tarasova, V. A. Korolev, V. P. Timofeev, Y. V. Tomilov, Angew. Chem. Int. Ed. 2014, 53, 3187;
12. Angew. Chem. 2014, 126, 3251.
13. Recent review:, K. C. Majumdar, RSC Adv. 2011, 1, 1152.
14. P. A. Wender, A. G. Correa, Y. Sato, R. Sun, J. Am. Chem. Soc. 2000, 122, 7815;
15. M. Potowski, J. O. Bauer, C. Strohmann, A. P. Antonchick, H. Waldmann, Angew. Chem. Int. Ed. 2012, 51, 9512;
16. Angew. Chem. 2012, 124, 9650;
17. Z.-L. He, H.-L. Teng, C.-J. Wang, Angew. Chem. Int. Ed. 2013, 52, 2934;
18. Angew. Chem. 2013, 125, 3006;
19. Z.-L. He, C.-J. Wang, Chem. Commun. 2015, 51, 534.
20. J. B. Hendrickson, J. S. Farina, J. Org. Chem. 1980, 45, 3361;
21. R. G. Arrayás, L. S. Liebeskind, J. Am. Chem. Soc. 2003, 125, 9026.
22. E. O. M. Orlemans, B. H. M. Lammerink, F. C. J. M. V. Veggel, W. Verboom, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1988, 53, 2278;
23. F. A. G. El-Essawy, S. M. Yassin, I. A. El-Sakka, A. F. Khattab, I. Søtofte, J. Ø. Madsen, A. Senning, J. Org. Chem. 1998, 63, 9840;
24. D. Garayalde, C. Nevado, ACS Catal. 2012, 2, 1462.
25. Y. Ueda, G. Roberge, V. Vinet, Can. J. Chem. 1984, 62, 2936;
26. H. M. L. Davies, Z.-Q. Peng, J. H. Houser, Tetrahedron Lett. 1994, 35, 8939.
27. X. Wang, X. Xu, P. Y. Zavalij, M. P. Doyle, J. Am. Chem. Soc. 2011, 133, 16402;
28. X. Xu, P. Y. Zavalij, M. P. Doyle, Angew. Chem. Int. Ed. 2013, 52, 12664;
29. Angew. Chem. 2013, 125, 12896;
30. X. Xu, P. Y. Zavalij, M. P. Doyle, J. Am. Chem. Soc. 2013, 135, 12439.
31. D. J. Lee, H. S. Han, J. Shin, E. J. Yoo, J. Am. Chem. Soc. 2014, 136, 11606.
32. N. Watanabe, T. Ogawa, Y. Ohtake, S. Ikegami, S. Hashimoto, Synlett 1996, 85;
33. H. Saito, H. Oishi, S. Kitagaki, S. Nakamura, M. Anada, S. Hashimoto, Org. Lett. 2002, 4, 3887;
34. C. G. Espino, K. W. Fiori, M. Kim, J. Du Bois, J. Am. Chem. Soc. 2004, 126, 15378;
35. R. P. Reddy, G. H. Lee, H. M. L. Davies, Org. Lett. 2006, 8, 3447;
36. J. R. Denton, D. Sukumaran, H. M. L. Davies, Org. Lett. 2007, 9, 2625;
37. A. DeAngelis, O. Dmitrenko, G. P. A. Yap, J. M. Fox, J. Am. Chem. Soc. 2009, 131, 7230;
38. A. G. Smith, H. M. L. Davies, J. Am. Chem. Soc. 2012, 134, 18241.
39. Yield was presumably increased by the adsorption of nitrogen gas on the molecular sieve., H. Verelst, G. V. Baron, J. Chem. Eng. Data 1985, 30, 66.
40. G. Song, D. Chen, Y. S. Han, C.-L. Pan, A. Jia, X. Li, Angew. Chem. Int. Ed. 2011, 50, 7791;
41. Angew. Chem. 2011, 123, 7937.