Nanosheet-enhanced enantioselectivity in the vanadium-catalyzed asymmetric epoxidation of allylic alcohols

Chemistry - A European Journal

Volumn 18, Issue 32, 2012, Pages 9911-9918

  Zhao, Li Wei ^a   Shi, Hui Min ^a   Wang, Jiu Zhao ^a   He, Jing ^a  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

asymmetric catalysis; heterogeneous catalysis; ligand design; nanosheets; substituent effects

Indexed keywords

ALLYLIC ALCOHOL; ASYMMETRIC CATALYSIS; ASYMMETRIC EPOXIDATION; CATALYTIC CENTER; CATALYTIC SITES; CHIRAL LIGAND; DFT CALCULATION; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; H-BONDING INTERACTION; INORGANIC LAYERS; LIGAND DESIGN; NATURALLY OCCURRING; SUBSTITUENT EFFECT; TRANSITION METAL CATALYSTS; TRANSITION STATE;

CATALYSIS; DENSITY FUNCTIONAL THEORY; LIGANDS; NANOSHEETS; STEREOCHEMISTRY; TRANSITION METALS; VANADIUM;

ENANTIOSELECTIVITY;

EID: 84864487715     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201659     Document Type: Article

References (58)

1. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keβeler, R. Stürmer, T. Zelinski, Angew. Chem. 2004, 116, 806-843
2. Angew. Chem. Int. Ed. 2004, 43, 788-824.
3. Y. Zhao, J. Rodrigo, A. H. Hoveyda, M. L. Snapper, Nature 2006, 443, 67-70.
4. J. M. Hawkins, T. J. N. Watson, Angew. Chem. 2004, 116, 3286-3290
5. Angew. Chem. Int. Ed. 2004, 43, 3224-3228.
6. J. T. Mohr, M. R. Krout, B. M. Stoltz, Nature 2008, 455, 323-332.
7. S. J. Malcolmson, S. J. Meek, E. S. Sattely, R. R. Schrock, A. H. Hoveyda, Nature 2008, 456, 933-937.
8. J. A. Enquist Jr, B. M. Stoltz, Nature 2008, 453, 1228-1231.
9. J. Streuff, D. E. White, S. C. Virgil, B. M. Stoltz, Nat. Chem. 2010, 2, 192-196.
10. J. García-Fortanet, F. Kessler, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 6676-6677.
11. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943.
12. S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875-5878.
13. N. Fleury-Brégeot, V. de La Fuente, S. Castillõn, C. Claver, ChemCatChem 2010, 2, 1346-1371.
14. J. Wieland, B. Breit, Nat. Chem. 2010, 2, 832-837.
15. M. Berthod, G. Mignani, G. Woodward, M. Lemaire, Chem. Rev. 2005, 105, 1801-1836.
16. S.-F. Zhu, Y. Cai, H.-X. Mao, J.-H. Xie, Q.-L. Zhou, Nat. Chem. 2010, 2, 546-551.
17. B. M. Trost, D. L. Van Vranken, C. Binge, J. Am. Chem. Soc. 1992, 114, 9327-9343.
18. W.-Q. Wu, Q. Peng, D.-X. Dong, X.-L. Hou, Y.-D. Wu, J. Am. Chem. Soc. 2008, 130, 9717-9725.
19. J. J. Miller, M. S. Sigman, Angew. Chem. 2008, 120, 783-786
20. Angew. Chem. Int. Ed. 2008, 47, 771-774.
21. M. P. Sibi, R. Zhang, S. Manyem, J. Am. Chem. Soc. 2003, 125, 9306-9307.
22. T. Hayashi, M. Kumada, Acc. Chem. Res. 1982, 15, 395-401.
23. M. M.-C. Lo, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 10270-10271.
24. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069.
25. S. Castillõn, C. Claver, Y. Díaz, Chem. Soc. Rev. 2005, 34, 702-713.
26. B. Zhao, X. Peng, Z. Wang, C. Xia, K. Ding, Chem. Eur. J. 2008, 14, 7847-7857.
27. H. Fernández-Pérez, P. Etayo, A. Panossian, A. Vidal-Ferran, Chem. Rev. 2011, 111, 2119-2176.
28. R. Gõmez Arrayás, J. Adrio, J. C. Carretero, Angew. Chem. 2006, 118, 7836-7878
29. Angew. Chem. Int. Ed. 2006, 45, 7674-7715.
30. T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691-1693.
31. J. Wang, L. Zhao, H. Shi, J. He, Angew. Chem. 2011, 123, 9337-9342
32. Angew. Chem. Int. Ed. 2011, 50, 9171-9176.
33. K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136-6137.
34. D. G. Evans, R. C. T. Slade, Struct. Bonding (Berlin) 2006, 119, 1-87.
35. P. J. Sideris, U. G. Nielsen, Z. Gan, C. P. Grey, Science 2008, 321, 113-117.
36. F. Cavani, F. Trifiro, A. Vaccari, Catal. Today 1991, 11, 173-301.
37. K. Severin, R. Bergs, W. Beck, Angew. Chem. 1998, 110, 1722-1743
38. Angew. Chem. Int. Ed. 1998, 37, 1634-1654.
39. J. Paradowska, M. Stodulski, J. Mlynarski, Angew. Chem. 2009, 121, 4352-4362
40. Angew. Chem. Int. Ed. 2009, 48, 4288-4297.
41. B.-F. Shi, N. Maugel, Y.-H. Zhang, J.-Q. Yu, Angew. Chem. 2008, 120, 4960-4964
42. Angew. Chem. Int. Ed. 2008, 47, 4882-4886.
43. S. Otto, J. B. F. N. Engberts, J. Am. Chem. Soc. 1999, 121, 6798-6806.
44. D. K. Friel, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2008, 130, 9942-9951.
45. L. C. Akullian, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2006, 128, 6532-6533.
46. A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785.
47. Z. Liu, R. Ma, M. Osada, N. Iyi, Y. Ebina, K. Takada, T. Sasaki, J. Am. Chem. Soc. 2006, 128, 4872-4880.
48. H. Shi, C. Yu, J. He, J. Catal. 2010, 271, 79-87.
49. R. M. Hanson, Chem. Rev. 1991, 91, 437-475.
50. M. Kakihana, T. Nagumo, M. Okamoto, H. Kakihana, J. Phys. Chem. 1987, 91, 6128-6136.
51. W. Zhang, A. Basak, Y. Kosugi, Y. Hoshino, H. Yamamoto, Angew. Chem. 2005, 117, 4463-4465
52. Angew. Chem. Int. Ed. 2005, 44, 4389-4391.
53. H. B. Henbest, R. A. L. Wilson, J. Chem. Soc. 1957, 1958-1965.
54. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
55. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.
56. J. B. Collins, P. v. R. Schleyer, J. S. Binkley, J. A. Pople, J. Chem. Phys. 1976, 64, 5142-5151.
57. R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem. Phys. 1971, 54, 724-728.
58. S. Aisawa, S. Takahashi, W. Ogasawara, Y. Umetsu, E. Narita, J. Solid State Chem. 2001, 162, 52-62.