Rhodium-catalyzed denitrogenative [2,3] sigmatropic rearrangement: An efficient entry to sulfur-containing quaternary centers

Chemistry - A European Journal

Volumn 19, Issue 45, 2013, Pages 15115-15119

  Yadagiri, Dongari ^a   Anbarasan, Pazhamalai ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

copper; quaternary centers; rhodium; sigmatropic rearrangement; sulfenylated imines

Indexed keywords

BUILDING BLOCKES; CHEMICAL BUILDING BLOCKS; CYCLOADDITION REACTION; QUATERNARY CENTERS; REGIOSELECTIVE FUNCTIONALIZATION; RHODIUM-CATALYZED; SIGMATROPIC REARRANGEMENTS; SULFENYLATED IMINES;

COPPER; CYCLOADDITION; NITROGEN COMPOUNDS; RHODIUM;

CATALYSIS;

COPPER; RHODIUM; SULFUR;

ARTICLE; CATALYSIS; CHEMISTRY; PROTEIN QUATERNARY STRUCTURE; QUATERNARY CENTERS; SIGMATROPIC REARRANGEMENT; SULFENYLATED IMINES;

COPPER; QUATERNARY CENTERS; RHODIUM; SIGMATROPIC REARRANGEMENT; SULFENYLATED IMINES;

CATALYSIS; PROTEIN STRUCTURE, QUATERNARY; RHODIUM; SULFUR;

EID: 84886641592     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302653     Document Type: Article

References (45)

1. B. Wang, Y. Q. Tu, Acc. Chem. Res. 2011, 44, 1207-1222
2. M. Bella, T. Gasperi, Synthesis 2009, 1583-1614
3. I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105-10146.
4. K. M. Cook, S. T. Hilton, J. Mecinovic, W. B. Motherwell, W. D. Figg, C. J. Schofield, J. Biol. Chem. 2009, 284, 26831-26838
5. K. L. Dormann, R. Bruckner, Angew. Chem. 2007, 119, 1178-1182
6. Angew. Chem. Int. Ed. 2007, 46, 1160-1163
7. S. Sawant, D. Youssef, A. Mayer, P. Sylvester, V. Wali, M. Arant, K. El Sayed, Chem. Pharm. Bull. 2006, 54, 1119-1123
8. R. K. Asthana, A. Srivastava, A. P. Singh, Deepali, S. P. Singh, G. Nath, R. Srivastava, B. S. Srivastava, J. Appl. Phycol. 2006, 18, 33-39.
9. B. M. Trost, Chem. Rev. 1978, 78, 363-382
10. B. M. Trost, Acc. Chem. Res. 1978, 11, 453-461.
11. N. De Kimpe, R. Verhe, L. De Buyck, N. Schamp, Synthesis 1983, 632-634.
12. W. Kirmse, M. Kapps, Chem. Ber. 1968, 101, 994-1003
13. M. P. Doyle, W. H. Tamblyn, V. Bagheri, J. Org. Chem. 1981, 46, 5094-5102.
14. Y. Zhang, J. Wang, Coord. Chem. Rev. 2010, 254, 941-953
15. Y. Li, Z. Huang, X. Wu, P.-F. Xu, J. Jin, Y. Zhang, J. Wang, Tetrahedron 2012, 68, 5234-5240
16. M. Liao, J. Wang, Green Chem. 2007, 9, 184
17. W. Pang, S. Zhu, H. Jiang, S. Zhu, Tetrahedron 2007, 63, 4543-4547
18. D. Crich, Y. Zou, F. Brebion, J. Org. Chem. 2006, 71, 9172-9177
19. M. Ma, L. Peng, C. Li, X. Zhang, J. Wang, J. Am. Chem. Soc. 2005, 127, 15016-15017
20. Y. Kato, K. Miki, F. Nishino, K. Ohe, S. Uemura, Org. Lett. 2003, 5, 2619-2621.
21. N. Mace, A. R. Thornton, S. B. Blakey, Angew. Chem. Int. Ed. 2013, 52, 5836-5839
22. A. R. Thornton, S. B. Blakey, J. Am. Chem. Soc. 2008, 130, 5020-5021.
23. T. L. Gilchrist, G. E. Gymer, Advances in Heterocyclic Chemistry 1974, 16, 33-85.
24. M. Regitz, Angew. Chem. 1965, 77, 428-428
25. Angew. Chem. Int. Ed. Engl. 1965, 4, 431-431
26. M. Regitz, Tetrahedron Lett. 1965, 6, 3287-3293.
27. S. Chuprakov, S. W. Kwok, V. V. Fokin, J. Am. Chem. Soc. 2013, 135, 4652-4655
28. M. Zibinsky, V. V. Fokin, Angew. Chem. Int. Ed. 2013, 52, 1507-1510
29. B. T. Parr, S. A. Green, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 4716-4718
30. E. E. Schultz, R. Sarpong, J. Am. Chem. Soc. 2013, 135, 4696-4699
31. J. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 6802-6805
32. T. Miura, T. Tanaka, T. Biyajima, A. Yada, M. Murakami, Angew. Chem. Int. Ed. 2013, 52, 3883-3886
33. J. S. Alford, H. M. L. Davies, Org. Lett. 2012, 14, 6020-6023
34. T. Miura, T. Biyajima, T. Fujii, M. Murakami, J. Am. Chem. Soc. 2012, 134, 194-196
35. N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi, V. V. Fokin, J. Am. Chem. Soc. 2012, 134, 14670-14673
36. T. Miura, Y. Funakoshi, M. Morimoto, T. Biyajima, M. Murakami, J. Am. Chem. Soc. 2012, 134, 17440-17443
37. N. Selander, B. T. Worrell, V. V. Fokin, Angew. Chem. Int. Ed. 2012, 51, 13054-13057
38. S. Chuprakov, J. A. Malik, M. Zibinsky, V. V. Fokin, J. Am. Chem. Soc. 2011, 133, 10352-10355
39. B. Chattopadhyay, V. Gevorgyan, Org. Lett. 2011, 13, 3746-3749; For review on transannulation of N-heterocycles see
40. B. Chattopadhyay, V. Gevorgyan, Angew. Chem. Int. Ed. 2012, 51, 862-872.
41. J. Raushel, V. V. Fokin, Org. Lett. 2010, 12, 4952-4955.
42. CCDC-933548 (4 aa) contains 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.
43. 4] catalyzed reactions did not afford any detectable enantioselectivity. This is probably due to the rearrangement from the free ylide and not from the metal-bound ylide and need of elevated reaction temperature, which allows the faster racemization of ylide; For a related reference, see:, X. Zhang, M. Ma, J. Wang, Tetrahedron: Asymmetry 2003, 14, 891-895.
44. O. Dimroth, Justus Liebigs Ann. Chem. 1909, 364, 183-226
45. O. Dimroth, W. Michaelis, Justus Liebigs Ann. Chem. 1927, 459, 39-46.