Reusable chiral macrocyclic Mn(III) salen complexes for enantioselective epoxidation of nonfunctionalized alkenes

Journal of Catalysis

Volumn 286, Issue , 2012, Pages 41-50

  Kureshy, Rukhsana I ^a   Roy, Tamal ^a   Khan, Noor Ul H ^a   Abdi, Sayed H R ^a   Sadhukhan, Arghya ^a   Bajaj, Hari C ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Chiral epoxides; Chiral Mn(III) macrocyclic salen complexes; Enantioselective; Kinetic investigation; Nonfunctionalized alkenes

Indexed keywords

ASYMMETRIC EPOXIDATION; CHIRAL EPOXIDES; CHROMENES; ENANTIOSELECTIVE; ENANTIOSELECTIVE EPOXIDATION; FIRST-ORDER DEPENDENCE; INITIAL CONCENTRATION; KINETIC INVESTIGATION; KINETIC INVESTIGATIONS; MACROCYCLICS; MN-SALEN; N-OXIDES; SALEN COMPLEX;

CATALYSTS; ENANTIOSELECTIVITY; MANGANESE; MASS SPECTROMETRY; OLEFINS; OPTICAL ROTATION; OXIDANTS; STYRENE;

SYNTHESIS (CHEMICAL);

EID: 84855584672     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2011.10.011     Document Type: Article

References (61)

1. R.V. Ottenbacher, K.P. Bryliakov, and E.P. Talsi Adv. Synth. Catal. 353 2011 885
2. R.V. Ottenbacher, K.P. Bryliakov, and E.P. Talsi Inorg. Chem. 49 2010 8620
3. G.D. Faveri, G. Ilyashenko, and M. Watkinson Chem. Soc. Rev. 40 2011 1722
4. F. Song, C. Wang, J.M. Falkowski, L. Ma, and W. Lin J. Am. Chem. Soc. 132 2010 15390
5. S. Liao, and B. List Angew. Chem., Int. Edit. 49 2010 628
6. R. Irie, K. Noda, Y. Ito, N. Matsumoto, and T. Katsuki Tetrahedron Lett. 31 1990 7345
7. W. Zhang, J.L. Loebach, S.R. Wilson, and E.N. Jacobson J. Am. Chem. Soc. 112 1990 2801
8. M. Wu, B. Wang, S. Wang, C. Xia, and W. Sun Org. Lett. 11 2009 3622
9. T. Katsuki Adv. Synth. Catal. 344 2002 131
10. E.M. McGarrigle, and D.G. Gilheany Chem. Rev. 105 2005 1563
11. T. Katsuki I. Ojima, Catalytic Asymmetric Synthesis second ed. 2000 Wiley-VCH New York 287
12. E.N. Jacobson, and M.H. Wu E.N. Jacobson, A. Pfaitz, H. Yamamoto, Comprehensive Asymmetric Catalysis vol. II 1999 Springer New York 649
13. H. Tanaka, H. Nishikawa, T. Uchida, and T. Katsuki J. Am. Chem. Soc. 132 2010 12034
14. A. Russo, and A. Lattanzi Org. Biomol. Chem. 8 2010 2633
15. X. Wang, and B. List Angew. Chem., Int. Ed. 47 2008 1119
16. C.G. Kokotos, E.M. Mcgarrigle, and V.K. Aggarwal Synlett 14 2008 2191
17. H. Wand, Z. Wang, and K. Ding Tetrahedron Lett. 50 2009 2200
18. E.N. Jacobsen I. Ojima, Asymmetric Epoxidation of Unfunctionalized Olefins 1993 VCH New York (Chapter 4.2, and references therein)
19. T. Hamada, K. Daikai, R. Irie, and T. Katsuki Tetrahedron 6 1995 2441
20. V. Schëurig, and F. Betschinger Chem. Rev. 92 1992 873
21. A. Martinez, C. Hemmert, and B. Meunier J. Catal. 234 2005 250
22. A. Martinez, C. Hemmert, C. Loup, G. Barre, and B. Meunier J. Org. Chem. 71 2006 1449
23. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, and R.V. Jasra Lawrence P. Bevy, Catalysis Research at the Cutting Edge 2005 Nova Science Publishers Inc. New York 115 133
24. K.C. Gupta, A.K. Sutar, and C.C. Lin Coordin. Chem. Rev. 253 2009 1926
25. A. Baleizão, and H. Garcia Chem. Rev. 106 2006 3987
26. A.S. Amarasekara, I.M. Neal, J. Murillo, D. Green, and A. Jennings Catal. Commun. 9 2008 2437
27. X. Tang, Y. Tang, G. Xu, S. Wei, and Y. Sun Catal. Commun. 10 2008 317
28. W. Ren, and X. Fu J. Mol. Catal. A 312 2009 40
29. S. Wei, Y. Tang, G. Xu, X. Tang, Y. Ling, R. Li, and Y. Sun React. Kinet. Catal. Lett. 97 2009 329
30. R. Tan, D. Yin, N. Yu, H. Zhao, and D. Yin J. Catal. 263 2009 284
31. X. Zou, X. Fu, Y. Li, X. Tu, S. Fu, Y. Luo, and X. Wu Adv. Synth. Catal. 352 2010 163
32. X. Tu, X. Fu, X. Hu, and Y. Li Inorg. Chem. Commun. 13 2010 404
33. K. Biernacka, A.R. Silva, A.P. Carvalho, J. Pires, and C. Freire Catal. Lett. 134 2010 63
34. R.I. Kureshy, I. Ahmad, N.H. Khan, S.H.R. Abdi, K. Pathak, and R.V. Jasra Tetrahedron: Asymmetry 16 2005 3562
35. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, I. Ahmad, S. Singh, and R.V. Jasra J. Catal. 221 2004 234
36. B.M. Choudary, T. Ramani, H. Maheswaran, L. Prashant, K.V.S. Ranganath, and K.V. Kumar Adv. Synth. Catal. 348 2006 493
37. S. Tangestaninejad, M. Moghadam, V. Mirkhani, I.M. Baltork, and M.S. Saeedi Appl. Catal. A. Gen. 381 2010 233
38. K.B.M. Jannsen, I. Laquire, W. Dehaen, R.F. Parton, I.F.J. Vankelecom, and P.A. Jacobs Tetrahedron: Asymmetry 8 1997 3481
39. C.E. Song, E.J. Roh, B.M. Yu, D.Y. Chi, S.C. Kim, and K.J. Lee J. Chem. Soc., Chem. Commun. 2000 837
40. L. Chen, F. Cheng, L. Jia, A. Zhang, J. Wu, and N. Tang Chirality 23 2011 69
41. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S.T. Patel, and R.V. Jasra Tetrahedron Lett. 42 2001 2915
42. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, A.P. Vyas, S. Singh, I. Ahmad, and R.V. Jasra J. Catal. 224 2004 229
43. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S. Singh, I. Ahmad, and R.V. Jasra J. Mol. Catal. 218 2004 141
44. N.C. Maity, S.H.R. Abdi, R.I. Kureshy, N.H. Khan, E. Suresh, G.P. Dangi, and H.C. Bajaj J. Catal. 277 2011 123
45. R. Bergmann, and R. Gericke J. Med. Chem. 33 1990 492
46. J.D. Godfrey Jr., R.H. Mueller, T.C. Sendergran, N. Soundararanjan, and V.J. Colandrea Tetrahedron Lett. 35 1994 6405
47. D.D. Perrin, W.L.F. Armarego, and D.R. Perrin Purification of Laboratory Chemicals 1981 Pergamon New York
48. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S.T. Patel, P.K. Iyer, P.S. Subramanian, and R.V. Jasra J. Catal. 209 2002 99
49. N.H. Khan, A. Sadhukhan, N.C. Maity, R.I. Kureshy, S.H.R. Abdi, S. Saravanan, and H.C. Bajaj Tetrahedron 67 2011 7073
50. X. Yao, H. Chen, W. Lii, G. Pan, X. Hu, and Z. Zheng Tetrahedron Lett. 41 2000 10
51. N.H. Khan, Santosh Agrawal, R.I. Kureshy, S.H.R. Abdi, K.J. Prathap, and R.V. Jasra Chirality 21 2008 262
52. M.K. Gurjar, B.V.N.B.S. Sarma, and A.V. Rama Rao Indian J. Chem. Sect. B 36 1997 213
53. W. Adam, C. Mock-Knoblauch, C.R. Saha-Möller, and M. Herderich J. Am. Chem. Soc. 122 2000 9685
54. C.H. Senanayake, G.B. Smith, K.M. Ryan, L.E. Fredenburgh, G. Liu, F.E. Roberts, D.L. Hughes, R.D. Larsen, T.R. Verhoeven, and P.J. Redier Tetrahedron Lett. 37 1996 3271
55. D.L. Hughes, G.B. Smith, J. Liu, G.C. Dezyeny, C.H. Senanayake, D.R. Larsen, T.R. Verhoeven, and P.J. Reider J. Org. Chem. 62 1997 2222
56. J.P. Collman, J.I. Brauman, B. Meunier, S.A. Raybuck, and T. Kodadek Proc. Natl. Acad. Sci. USA 81 1984 3245
57. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S. Singh, I. Ahmed, R.S. Shukla, and R.V. Jasra J. Catal. 219 2003 1
58. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, and K.N. Bhatt Tetrahedron: Asymmetry 1 1993 1693
59. C. Linde, M. Arnold, P. Norrby, and B. kermark Angew. Chem., Int. Ed. 36 1997 1723
60. C. Linde, B. kermark, P. Norrby, and M. Svensson J. Am. Chem. Soc. 121 1999 5083
61. K. Srinivasan, P. Michaud, and J.K. Kochi J. Am. Chem. Soc. 108 1986 2309