Elucidating steric effects on enantioselective epoxidation catalyzed by (salen)Mn in metal-organic frameworks

Journal of Molecular Catalysis A: Chemical

Volumn 334, Issue 1-2, 2011, Pages 89-97

  Oxford, Gloria A E ^a   Dubbeldam, David ^b   Broadbelt, Linda J ^a   Snurr, Randall Q ^a  

^a Northwestern University   (United States)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

(Salen)Mn; Enantioselective oxidation; Metal organic framework; Molecular modeling

Indexed keywords

(SALEN)MN; ACTIVE SITE; ASYMMETRIC INDUCTION; ATOMISTIC MODELING; ENANTIOSELECTIVE EPOXIDATION; ENANTIOSELECTIVE OXIDATION; HETEROGENEOUS CATALYST; HIGH ENANTIOSELECTIVITY; HIGHLY SENSITIVE; HOMOGENEOUS CATALYST; INTERPENETRATED FRAMEWORKS; METAL-ORGANIC FRAMEWORK; ROTATIONAL ENERGY; STERIC EFFECT;

CHIRALITY; ENANTIOMERS; ENANTIOSELECTIVITY; MANGANESE; METALS; MOLECULAR MODELING; OXIDATION; RHENIUM; STEREOCHEMISTRY;

CATALYSTS;

EID: 78650517559     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2010.11.001     Document Type: Article

References (43)

1. E.M. McGarrigle, and D.G. Gilheany Chem. Rev. 105 2005 1563 1602
2. E.N. Jacobsen, W. Zhang, and M.L. Guler J. Am. Chem. Soc. 113 1991 6703 6704
3. T. Katsuki Coord. Chem. Rev. 140 1995 189 214
4. T. Katsuki Adv. Synth. Catal. 344 2002 131 147
5. H. Jacobsen, and L. Cavallo Chem. Eur. J. 7 2001 800 807
6. K.N. Houk, N.C. DeMello, K. Condroski, J. Fennen, and T. Kasuga Origins of enantioselection in Jacobsen epoxidations Electronic Conference on Heterocyclic Chemistry (ECHET96) London 1996
7. N. Hosoya, A. Hatayama, K. Yanai, H. Fujii, R. Irie, and T. Katsuki Synlett 1993 1993 641 645
8. T. Hamada, R. Irie, and T. Katsuki Synlett 1994 1994 479 481
9. E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker, and L. Deng J. Am. Chem. Soc. 113 1991 7063 7064
10. P.J. Pospisil, D.H. Carsten, and E.N. Jacobsen Chem. Eur. J. 2 1996 974 980
11. T. Hashihayata, T. Punniyamurthy, R. Irie, T. Katsuki, M. Akita, and Y. Moro-oka Tetrahedron 55 1999 14599 14610
12. Y.N. Ito, and T. Katsuki Bull. Chem. Soc. Jpn. 72 1999 603 619
13. W. Zhang, J.L. Loebach, S.R. Wilson, and E.N. Jacobsen J. Am. Chem. Soc. 112 1990 2801 2803
14. K. Malek, A.P.J. Jansen, C. Li, and R.A. van Santen J. Catal. 246 2007 127 135
15. S.-H. Cho, B. Ma, S.T. Nguyen, J.T. Hupp, and T.E. Albrecht-Schmitt Chem. Commun. 2006 2563 2565
16. G.A.E. Oxford, R.Q. Snurr, and L.J. Broadbelt Ind. Eng. Chem. Res. 49 2010 10965 10973
17. D. Dubbeldam, S. Calero, D.E. Ellis, and R.Q. Snurr RASPA 1.0 2008 Northwestern University Evanston
18. D. Dubbeldam, G.A.E. Oxford, R. Krishna, L.J. Broadbelt, and R.Q. Snurr J. Chem. Phys. 133 2010 034114
19. J.P. Perdew Phys. Rev. B 33 1986 8822 8824
20. A.D. Becke Phys. Rev. A 38 1988 3098 3100
21. A. Schäfer, C. Huber, and R. Ahlrichs J. Chem. Phys. 100 1994 5829 5835
22. A. Schäfer, H. Horn, and R. Ahlrichs J. Chem. Phys. 97 1992 2571 2577
23. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, 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, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian03 2004 Gaussian, Inc. Wallingford, CT
24. C.M. Breneman, and K.B. Wiberg J. Comput. Chem. 11 1990 361 373
25. J. Baker J. Comput. Chem. 7 1986 385 395
26. D. Dubbeldam, R. Krishna, and R.Q. Snurr J. Phys. Chem. C 113 2009 19317 19327
27. A.R. Leach Molecular Modelling: Principles and Applications 2nd ed. 2001 Pearson Education Harlow, Essex, UK
28. H.C. Andersen J. Comput. Phys. 52 1983 24 34
29. D. Gao, S. Schefzick, and K.B. Lipkowitz J. Am. Chem. Soc. 121 1999 9481 9482
30. K.B. Lipkowitz, S. Schefzick, and D. Avnir J. Am. Chem. Soc. 123 2001 6710 6711
31. S. Alvarez, S. Schefzick, K. Lipkowitz, and D. Avnir Chem. Eur. J. 9 2003 5832 5837
32. S. Alvarez, P. Alemany, and D. Avnir Chem. Soc. Rev. 34 2005 313 326
33. H. Zabrodsky, and D. Avnir J. Am. Chem. Soc. 117 1995 462 473
34. M. Pinsky, C. Dryzun, D. Casanova, P. Alemany, and D. Avnir J. Comput. Chem. 29 2008 2712 2721
35. K.B. Lipkowitz, and S. Schefzick Chirality 14 2002 677 682
36. http://www.csm.huji.ac.il/new/
37. N.H. Lee, A.R. Muci, and E.N. Jacobsen Tetrahedron Lett. 32 1991 5055 5058
38. T. Katsuki Synlett 2003 281 297
39. K. Seki Phys. Chem. Chem. Phys. 4 2002 1968 1971
40. B. Chen, S. Ma, F. Zapata, E.B. Lobkovsky, and J. Yang Inorg. Chem. 45 2006 5718 5720
41. T.K. Maji, R. Matsuda, and S. Kitagawa Nat. Mater. 6 2007 142 148
42. K.L. Mulfort, O.K. Farha, C.D. Malliakas, M.G. Kanatzidis, and J.T. Hupp Chem. Eur. J. 16 2010 276 281
43. Y.-S. Bae, D. Dubbeldam, A. Nelson, K.S. Walton, J.T. Hupp, and R.Q. Snurr Chem. Mater. 21 2009 4768 4777