Flavin-cyclodextrin conjugates: Effect of the structure on the catalytic activity in enantioselective sulfoxidations

Tetrahedron Asymmetry

Volumn 23, Issue 22-23, 2012, Pages 1571-1583

  Hartman, Tomáš ^a   Herzig, Vladimír ^a,b   Buděšínský, Miloš ^b   Jindřich, Jindřich ^c   Cibulka, Radek ^a   Kraus, Tomáš ^b  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOXAZINIUM; ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; HYDROGEN PEROXIDE; ISOALLOXAZINIUM; MACROCYCLIC COMPOUND; QUERCETIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONJUGATE; CONTROLLED STUDY; CYCLIZATION; ENANTIOSELECTIVITY; ETHERIFICATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION TIME; SULFOXIDATION; SYNTHESIS;

EID: 84870278571     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.10.017     Document Type: Article

References (48)

1. R. Noyori, M. Aoki, and K. Sato Chem. Commun. 2003 1977 1986.
2. A. Russo, C. De Fusco, and A. Lattanzi ChemCatChem 4 2012 901 916.
3. E. Bäckvall Modern Oxidation Methods 2010 Wiley-VCh Weinheim.
4. M.C. Carreno, G. Hernandez-Torres, M. Ribagorda, and A. Urbano Chem. Commun. 46 2009 6129 6144.
5. J. Legros, J.R. Dehli, and C. Bolm Adv. Synth. Catal. 347 2005 19 31.
6. S. Caron, R.W. Dugger, S.G. Ruggeri, J.A. Ragan, and D.H.B. Ripin Chem. Rev. 106 2006 2943 2989.
7. E. Wojaczynska, and J. Wojaczynski Chem. Rev. 110 2010 4303 4356.
8. I. Fernandez, and N. Khiar Chem. Rev. 103 2003 3651 3705.
9. K.P. Bryliakov, and E.P. Talsi Curr. Org. Chem. 12 2008 386 404.
10. H.B. Kagan Organosulfur Chemistry in Asymmetric Synthesis 2008 Wiley-VCH Weinheim.
11. J. Fujisaki, K. Matsumoto, and T. Katsuki J. Am. Chem. Soc. 133 2011 56 61.
12. Y. Wu, J. Liu, X. Li, and A.S.C. Chan Eur. J. Org. Chem. 2009 2607 2610.
13. C. Drago, L. Caggiano, and R.F.W. Jackson Angew. Chem. 44 2005 7221 7223.
14. Q. Zeng, H. Wang, T. Wang, Y. Cai, W. Weng, and Y. Zhao Adv. Synth. Catal. 347 2005 1933 1936.
15. K. Matsumoto, T. Yamaguchi, and T. Katsuki Chem. Commun. 2008 1704 1706.
16. T. Yamaguchi, K. Matsumoto, B. Saito, and T. Katsuki Angew. Chem., Int. Ed. 46 2007 4729 4731.
17. J. Legros, and C. Bolm Angew. Chem. 42 2003 5487 5489.
18. J. Legros, and C. Bolm Angew. Chem. 43 2004 4225 4228.
19. J. Legros, and C. Bolm Chemistry 11 2005 1086 1092.
20. H. Egami, and T. Katsuki Synlett 2008 1543 1546.
21. A. Scarso, and G. Strukul Adv. Synth. Catal. 347 2005 1227 1234.
22. A. Massa, V. Mazza, and A. Scettri Tetrahedron: Asymmetry 16 2005 2271 2275.
23. H. Egami, and T. Katsuki J. Am. Chem. Soc. 129 2007 8940 8941.
24. K. Matsumoto, T. Yamaguchi, J. Fujisaki, B. Saito, and T. Katsuki Chem. Asian J. 3 2008 351 358.
25. H. Tanaka, H. Nishikawa, T. Uchida, and T. Katsuki J. Am. Chem. Soc. 132 2010 12034 12041.
26. J. Sun, C. Zhu, Z. Dai, M. Yang, Y. Pan, and H. Hu J. Org. Chem. 69 2004 8500 8503.
27. K.A. Stingl, and S.B. Tsogoeva Tetrahedron: Asymmetry 21 2010 1055 1074.
28. A. Armstrong Enantioselective Organocatalysis 2007 Wiley-VCH Weinheim.
29. S. Shinkai, T. Yamaguchi, O. Manabe, and F. Toda J. Chem. Soc., Chem. Commun. 1988 1399 1401.
30. S.I. Murahashi Angew. Chem., Int. Ed. 34 1995 2443 2465.
31. R. Jurok, R. Cibulka, H. Dvořáková, F. Hampl, and J. Hodačová Eur. J. Org. Chem. 2010 5217 5224.
32. V. Mojr, V. Herzig, M. Buděšínský, R. Cibulka, and T. Kraus Chem. Commun. 46 2010 7599 7601.
33. V. Mojr, M. Buděšínský, R. Cibulka, and T. Kraus Org. Biomol. Chem. 9 2011 7318 7326.
34. F.G. Gelalcha Chem. Rev. 107 2007 3338 3361.
35. S. Ghisla, and V. Massey Eur. J. Biochem. 181 1989 1 17.
36. M.J.H. Moonen, M.W. Fraaije, I. Rietjens, C. Laane, and W.J.H. van Berkel Adv. Synth. Catal. 344 2002 1023 1035.
37. P. Ménová, and R. Cibulka J. Mol. Catal. A: Chem. 363-364 2012 362 370.
38. Z.-M. Liu, H. Zhao, M.-Q. Li, Y.-B. Lan, Q.-B. Yao, J.-C. Tao, and X.-W. Wang Adv. Synth. Catal. 354 2012 1012 1022.
39. S. Liao, I. Čorić, Q. Wang, and B. List J. Am. Chem. Soc. 134 2012 10765 10768.
40. K. Kino, T. Kobayashi, E. Arima, R. Komori, and H. Miyazawa Bioorg. Med. Chem. Lett. 19 2009 2070 2074.
41. J. Takeda, S. Ohta, and M. Hirobe J. Am. Chem. Soc. 109 1987 7677 7688.
42. S. Youssef, and W. Pfleiderer J. Heterocycl. Chem. 35 1998 949 954.
43. F. Yoneda, Y. Sakuma, M. Ichiba, and K. Shinomura J. Am. Chem. Soc. 98 1976 830 835.
44. J. Jindřich, and I. Tišlerová J. Org. Chem. 70 2005 9054 9055.
45. R. Cibulka, L. Baxová, H. Dvořáková, F. Hampl, P. Ménová, V. Mojr, B. Plancq, and S. Sayin Collect. Czech. Chem. Commun. 74 2009 973 993.
46. Y. Imada, H. Iida, S. Ono, and S.-I. Murahashi J. Am. Chem. Soc. 125 2003 2868 2869.
47. R.C. Petter, J.S. Salek, C.T. Sikorski, G. Kumaravel, and F.T. Lin J. Am. Chem. Soc. 112 1990 3860 3868.
48. M. Deshmukh, E. Dunach, S. Juge, and H.B. Kagan Tetrahedron Lett. 25 1984 3467 3470.