Rh(II)-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides derived from N-tosylhydrazones and sulfides

Tetrahedron

Volumn 68, Issue 26, 2012, Pages 5234-5240

  Li, Yuye ^a,b   Huang, Zhongxing ^a   Wu, Xinhu ^a,b   Xu, Peng Fei ^b   Jin, Jing ^b   Zhang, Yan ^a,b   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

2,3 Sigmatropic rearrangement; Allylic phenyl sulfides; N Tosylhydrazone; Propargyl phenyl sulfides; Sulfur ylides

Indexed keywords

ALDEHYDE; ALLYL PHENYL SULFIDE; ALLYL SULFIDE; CYCLOBUTENONE; CYCLOPROPANE; FUNCTIONAL GROUP; KETONE; N TOSYLHYDRAZONE; PROPARGYL PHENYL SULFIDE; RHODIUM; SULFIDE; SULFUR; SULFUR YLIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; PRIORITY JOURNAL; SIGMATROPIC REARRANGEMENT;

EID: 84861659591     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.032     Document Type: Article

References (52)

1. E. Vedejs Acc. Chem. Res. 17 1984 358
2. A.-H. Li, L.-X. Dai, and V.K. Aggarwal Chem. Rev. 97 1997 2341
3. M. Mitani, M.T. Tsuchida, and K. Koyama J. Chem. Soc., Chem. Commun. 1974 869
4. B.M. Trost, and L.S. Melvin Jr. Sulfur Ylides 1975 Academic New York, NY Chapter 7
5. R. Berger, J.W. Ziller, and D.L. Van Vranken J. Am. Chem. Soc. 120 1998 841
6. A. Padwa, and J.R. Gasdaska J. Org. Chem. 51 1986 2857
7. W. Kirmse, and M. Kapps Chem. Ber. 101 1968 994
8. M.P. Doyle, W.H. Tamblyn, and V. Bagheri J. Org. Chem. 46 1981 5094
9. M.P. Doyle, J.H. Griffin, M.S. Chinn, and D. van Leusen J. Org. Chem. 49 1984 1917
10. D.M. Hodgson, T.M. Pierard, and P.A. Stupple Chem. Soc. Rev. 30 2001 50
11. G. Mehta, and S. Muthusamy Tetrahedron 58 2002 9477
12. W. Ando, and H. Matsuyama Nitrogen, Oxygen Sulfur Ylide Chem. 2002 163
13. S. Braverman, and M. Cherkinsky Top. Curr. Chem. 275 2007 67
14. M. Reggelin Top. Curr. Chem. 275 2007 1
15. J. Wang D.M.P. Mingos, R.H. Crabtree, Applications II: Transition Metal Compounds in Organic Synthesis 2 Vol. 11 2007 Elsevier Oxford 151
16. Y. Zhang, and J. Wang Coord. Chem. Rev. 254 2010 941
17. X. Zhang, M. Ma, and J. Wang Tetrahedron: Asymmetry 14 2003 891
18. X. Zhang, M. Ma, and J. Wang Chin. J. Chem. 21 2003 878
19. Y. Kato, K. Miki, F. Nishino, K. Ohe, and S. Uemura Org. Lett. 5 2003 2619
20. M. Ma, L. Peng, C. Li, X. Zhang, and J. Wang J. Am. Chem. Soc. 127 2005 15016
21. D. Crich, Y. Zou, and F. Brebion J. Org. Chem. 71 2006 9172
22. A.V. Stepakov, A.P. Molchanov, J. Magull, D. Vidovic, G.L. Starova, J. Kopf, and R.R. Kostikov Tetrahedron 62 2006 3610
23. W. Pang, S. Zhu, H. Jiang, and S. Zhu Tetrahedron 63 2007 4543
24. M. Liao, and J. Wang Green Chem. 9 2007 184
25. L. Peng, X. Zhang, M. Ma, and J. Wang Angew. Chem., Int. Ed. 46 2007 1905
26. M. Liao, L. Peng, and J. Wang Org. Lett. 10 2008 693
27. Y. Li, Y. Shi, Z. Huang, X. Wu, P. Xu, J. Wang, and Y. Zhang Org. Lett. 13 2011 1210
28. T. Ye, and M.A. McKervey Chem. Rev. 94 1994 1091
29. A. Padwa, and M.D. Weingarten Chem. Rev. 96 1996 223
30. M.P. Doyle, M.A. McKervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds 1998 Wiley-Interscience New York, NY
31. A. Padwa Chem. Commun. 1998 1417
32. A. Padwa J. Organomet. Chem. 617-618 2001 3
33. V.K. Aggarwal, and C.L. Winn Acc. Chem. Res. 37 2004 611
34. A.G.H. Wee Curr. Org. Synth. 3 2006 499
35. W.R. Bamford, and T.S.M. Stevens J. Chem. Soc. 1952 4735
36. R.H. Shapiro Org. React. 23 1976 405
37. R.M. Adlington, and A.G.M. Barrett Acc. Chem. Res. 16 1983 55
38. J.R. Fulton, V.K. Aggarwal, and J. de Vicente Eur. J. Org. Chem. 2005 1479
39. J.L. Zhang, P.W.H. Chan, and C.M. Che Tetrahedron Lett. 44 2003 8733
40. M.P. Doyle, and M. Yan J. Org. Chem. 67 2002 602
41. J. Barluenga, P. Moriel, C. Valdés, and F. Aznar Angew. Chem., Int. Ed. 46 2007 5587
42. Q. Xiao, J. Ma, Y. Yang, Y. Zhang, and J. Wang Org. Lett. 11 2009 4732
43. J. Barluenga, M. Escribano, P. Moriel, F. Aznar, and C. Valdés Chem. - Eur. J. 15 2009 13291
44. L. Zhou, F. Ye, Y. Zhang, and J. Wang J. Am. Chem. Soc. 132 2010 13590
45. Q. Xiao, Y. Xia, H. Li, Y. Zhang, and J. Wang Angew. Chem., Int. Ed. 50 2011 1114
46. L. Zhou, F. Ye, J. Ma, Y. Zhang, and J. Wang Angew. Chem., Int. Ed. 50 2011 3510
47. J. Barluenga, and C. Valdés Angew. Chem., Int. Ed. 50 2011 7486
48. Z. Shao, and H. Zhang Chem. Soc. Rev. 41 2012 560
49. B. Corbel, J. Decesare, and T. Durst Can. J. Chem. 56 1978 505
50. J. Decesare, B. Corbel, and T. Durst Can. J. Chem. 59 1981 1415
51. B. Corbel, and T. Durst J. Org. Chem. 41 1976 3648
52. K. Chiba, R. Uchiyama, S. Kim, Y. Kitano, and M. Tada Org. Lett. 3 2001 1245