Diastereoselective synthesis of tetrahydrofurano- and tetrahydropyrano-dihydropyrroles containing N,O-acetal moieties via rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with oxacycloalkenes

Advanced Synthesis and Catalysis

Volumn 357, Issue 1, 2014, Pages 210-220

  Kim, Cheol Eui ^a   Park, Youngchul ^a   Park, Sangjune ^a   Lee, Phil Ho ^a  

^a Kangwon National University   (South Korea)

Author keywords

Dihydropyrrole; Homogeneous catalysis; N sulfonyl triazole; Rhodium; Transannulation

Indexed keywords

EID: 84920734672     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400604     Document Type: Short Survey

References (42)

1. a) A.W. G. Burgett, Q. Li, Q. Wei, P. G. Harran, Angew. Chem. 2003, 115, 5111;
2. Angew. Chem. Int. Ed. 2003, 42, 4961;
3. b) N. Lindquist, W. Fenical, G. D. Van Duyne, J. Cjardy, J. Am. Chem. Soc. 1991, 113, 2303;
4. c) J. Li, A.W. Burgett, L. Esser, C. Amezscusa, P. G. Harran, Angew. Chem. 2001, 113, 4906;
5. Angew. Chem. Int. Ed. 2001, 40, 4770.
6. Q.-X. Wu, M. S. Crews, M. Draskovic, J. Sohn, T. A. Johnson, K. Tenney, F. A. Valeriote, X.-J. Yao, L. F. Bjeldanes, P. Crews, Org. Lett. 2010, 12, 4458.
7. T.-S. Kam, S.-J. Tan, S.-W. Ng, K. Komiyama, Org. Lett. 2008, 10, 3749.
8. a) W.-H. Chiou, C.-L. Kao, J.-C. Tsai, Y.-M. Chang, Chem. Commun. 2013, 49, 8232;
9. b) M. S. Morales-Ríos, N. F. Santos-Sánchez, P. Joseph-Nathan, J. Nat. Prod. 2002, 65, 136;
10. c) A. S. EIAzab, T. Taniguchi, K. Ogasawara, Org. Lett. 2000, 2, 2757.
11. D. Yamamoto, T. Sunazuka, T. Hirose, N. Kojima, E. Kaji, S. Omura, Bioorg. Med. Chem. Lett. 2006, 16, 2807.
12. R. Beaud, R. Guillot, C. Kouklovsky, G. Vincent, Angew. Chem. 2012, 124, 12714;
13. Angew. Chem. Int. Ed. 2012, 51, 12546.
14. a) H. M. L. Davies, J. S. Alford, Chem. Soc. Rev. 2014, 43, 5151 and references therein:
15. b) T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 14972;
16. c) T. Miura, M. Yamauchi, M. Murakami, Chem. Commun. 2009, 1470;
17. d) B. Chattopadhyay, V. Gevorgyan, Org. Lett. 2011, 13, 3746;
18. e) Y. Shi, V. Gevorgyan, Org. Lett. 2013, 15, 5394;
19. f) T. Miura, K. Hiraga, T. Biyajima, T. Nakamuro, M. Murakami, Org. Lett. 2013, 15, 3298;
20. g) E. E. Schultz, R. Sarpong, J. Am. Chem. Soc. 2013, 135, 4696;
21. h) S. Chuprakov, S. W. Kwok, V. V. Fokin, J. Am. Chem. Soc. 2013, 135, 4652;
22. i) B. T. Parr, S. A. Green, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 4716;
23. j) M. Zibinsky, V. V. Fokin, Angew. Chem. 2013, 125, 1547;
24. Angew. Chem. Int. Ed. 2013, 52, 1507;
25. k) J. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 6802;
26. l) T. Miura, Y. Funakoshi, M. Murakami, J. Am. Chem. Soc. 2014, 136, 2272;
27. m) S. W. Kwok, L. Zhang, N. P. Grimster, V. V. Fokin, Angew. Chem. 2014, 126, 3520;
28. Angew. Chem. Int. Ed. 2014, 53, 3452;
29. n) M. Zibinsky, V. V. Fokin, Org. Lett. 2011, 13, 4870;
30. o) J. S. Alford, J. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 11712.
31. a) C.-E. Kim, S. Park, D. Eom, B. Seo, P. H. Lee, Org. Lett. 2014, 16, 1900;
32. b) S. Kim, J. Mo, J. Kim, T. Ryu, P. H. Lee, Asian. J. Org. Chem. 2014, 3, 926;
33. c) S. Park, W.-S. Yong, S. Kim, P. H. Lee, Org. Lett. 2014, 16, 4468.
34. Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif.
35. Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif.
36. a) T. J. Donohoe, A. J. Orr, K. Gosby, M. Bingham, Eur. J. Org. Chem. 2005, 1969;
37. b) K. Sakai, M. Suzuki, K.-I. Nunami, N. Yoneda, Y. Onoda, Y. Iwasawa, Chem. Pharm. Bull. 1980, 28, 2384;
38. c) T. Dohi, K. Morimoto, Y. Kiyono, H. Tohma, Y. Kita, Org. Lett. 2005, 7, 537;
39. d) T. J. Donohoe, N. M. Kershaw, A. J. Orr, K. M. P. Wheelhouse, L. P. Fishlock, A. R. Lacy, M. Bingham, P. A. Procopiou, Tetrahedron 2008, 64, 809;
40. e) P. W. Davies, N. Martin, Org. Lett. 2009, 11, 2293.
41. T. H. Wöste, M. Oestreich, Chem. Eur. J. 2011, 17, 11914.
42. H. Braun, O. Nuyken, Des. Monomers Polym. 2001, 4, 19.