Critical role of external axial ligands in chirality amplification of trans-cyclohexane-1,2-diamine in salen complexes

Journal of the American Chemical Society

Volumn 131, Issue 34, 2009, Pages 12394-12405

  Kurahashi, Takuya ^a   Hada, Masahiko ^b   Fujii, Hiroshi ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AXIAL LIGAND; CHIRAL SCAFFOLDS; CIRCULAR DICHROISM; CONFORMATIONAL PROPERTIES; DIAMINE MOIETIES; GAIN INSIGHT; PLANAR CONFORMATIONS; PLANAR SOLIDS; QUANTUM-CHEMICAL CALCULATION; SALEN COMPLEX; SALEN LIGANDS; SOLUTION CONFORMATIONS; SYMMETRY ADAPTED CLUSTERS; TRANS-CYCLOHEXANE; X RAY CRYSTAL STRUCTURES;

AMINES; AMPLIFICATION; CHIRALITY; CHLORINE COMPOUNDS; CYCLOHEXANE; DICHROISM; ENANTIOMERS; LIGANDS; MANGANESE; MANGANESE COMPOUNDS; QUANTUM CHEMISTRY; STEREOCHEMISTRY;

CONFORMATIONS;

CHLORIDE; DIAMINE DERIVATIVE; HYDROGEN; LIGAND; MANGANESE; METAL COMPLEX; NITRIC OXIDE; NITROGEN; OXYGEN; SALICYLIC ACID DERIVATIVE; SCAFFOLD PROTEIN; TRANS CYCLOHEXANE 1,2 DIAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; QUANTUM CHEMISTRY; RING OPENING; SOLID STATE; SOLUTION AND SOLUBILITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXYLAMINES; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; SOLUTIONS; STEREOISOMERISM;

EID: 69349103330     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904635n     Document Type: Article

References (71)

1. (a) Atwood, D. A.; Harvey, M. J. Chem. Rev. 2001, 101, 37-52.
2. (b) Cozzi, P. G. Chem. Soc. Rev. 2004, 33, 410-421.
3. (a) Canali, L.; Sherrington, D. C. Chem. Soc. Rev. 1999, 28, 85-93.
4. (b) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
5. Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Chem. Commun. 2002, 919-927.
6. Irie, R.; Katsuki, T. Chem. Rec. 2004, 4, 96-109.
7. (e) Katsuki, T. Chem. Soc. Rev. 2004, 33, 437-444.
8. (f) McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563-1602.
9. (g) Baleizão, C.; Garcia, H. Chem. Rev. 2006, 106, 3987-4043.
10. (h) Matsumoto, K.; Saito, B.; Katsuki, T. Chem. Commun. 2007, 3619-3627.
11. (a) Wu, A. J.; Penner-Hahn, J. E.; Pecoraro, V. L. Chem. Rev. 2004, 104, 903-938.
12. (b) Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L., Jr. Chem. Rev. 2004, 104, 939-986.
13. Darensbourg, D. J. Chem. Rev. 2007, 107, 2388-2410.
14. (a) Muller, J. G.; Kayser, L. A.; Paikoff, S. J.; Duarte, V.; Tang, N.; Perez, R. J.; Rokita, S. E.; Burrows, C. J. Coord. Chem. Rev. 1999, 185-186, 761-774.
15. (b) Thompson, K. H.; McNeill, J. H.; Orvig, C. Chem. Rev. 1999, 99, 2561-2571.
16. Riley, D. P. Chem. Rev. 1999, 99, 2573-2587.
17. (a) Miyasaka, H.; Saitoh, A.; Abe, S. Coord. Chem. Rev. 2007, 251, 2622-2664.
18. (b) Wezenberg, S. J.; Kleij, A. W. Angew. Chem., Int. Ed. 2008, 47, 2354-2364.
19. Kleij, A. W. Chem. - Eur. J. 2008, 14, 10520-10529.
20. Wang, Y.; DuBois, J. L.; Hedman, B.; Hodgson, K. O.; Stack, T. D. P. Science 1998, 279, 537-540.
21. Hormnirun, P.; Marshall, E. L.; Gibson, V. C.; Pugh, R. I.; White, A. J. P. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15343-15348.
22. Kim, H.-J.; Kim, W.; Lough, A. J.; Kim, B. M.; Chin, J. J. Am. Chem. Soc. 2005, 127, 16776-16777.
23. Watanabe, A.; Uchida, T.; Irie, R.; Katsuki, T. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5737-5742.
24. Dong, Z.; Karpowicz, R. J., Jr.; Bai, S.; Yap, G. P. A.; Fox, J. M. J. Am. Chem. Soc. 2006, 128, 14242-14243.
25. Wiznycia, A. V.; Desper, J.; Levy, C. J. Inorg. Chem. 2006, 45, 10034-10036.
26. Akine, S.; Taniguchi, T.; Nabeshima, T. J. Am. Chem. Soc. 2006, 128, 15765-15774.
27. Heo, J.; Jeon, Y.-M.; Mirkin, C. A. J. Am. Chem. Soc. 2007, 129, 7712-7713.
28. Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691-1693.
29. Bobb, R.; Alhakimi, G.; Studnicki, L.; Lough, A.; Chin, J. J. Am. Chem. Soc. 2002, 124, 4544-4545.
30. (a) Fallis, I. A.; Murphy, D. M.; Willock, D. J.; Tucker, R. J.; Farley, R. D.; Jenkins, R.; Strevens, R. R. J. Am. Chem. Soc. 2004, 126, 15660-15661.
31. (b) Murphy, D. M.; Fallis, I. A.; Willock, D. J.; Landon, J.; Carter, E.; Vinck, E. Angew. Chem., Int. Ed. 2008, 47, 1414-1416.
32. Dong, Z.; Yap, G. P. A.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 11850-11853.
33. Kemper, S.; Hrobárik, P.; Kaupp, M.; Schlörer, N. E. J. Am. Chem. Soc. 2009, 131, 4172-4173.
34. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161-3195.
35. (a) Pospisil, P. J.; Carsten, D. H.; Jacobsen, E. N. Chem. - Eur. J. 1996, 2, 974-980.
36. (b) Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924-10925.
37. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 6086-6087.
38. (a) Kurahashi, T.; Kobayashi, Y.; Nagatomo, S.; Tosha, T.; Kitagawa, T.; Fujii, H. Inorg. Chem. 2005, 44, 8156-8166.
39. (b) Kurahashi, T.; Kikuchi, A.; Tosha, T.; Shiro, Y.; Kitagawa, T.; Fujii, H. Inorg. Chem. 2008, 47, 1674-1686.
40. Kurahashi, T.; Fujii, H. Inorg. Chem. 2008, 47, 7556-7567.
41. (a) Bryliakov, K. P.; Babushkin, D. E.; Talsi, E. P. J. Mol. Catal. A 2000, 158, 19-35.
42. (b) Adam, W.; Mock-Knoblauch, C.; Saha-Möller, C. R.; Herderich, M. J. Am. Chem. Soc. 2000, 122, 9685-9691.
43. Campbell, K. A.; Lashley, M. R.; Wyatt, J. K.; Nantz, M. H.; Britt, R. D. J. Am. Chem. Soc. 2001, 123, 5710-5719.
44. For proposed conformations of Mn(salen), see ref 2f.
45. Weak CD for (R,R)-3 is not due to racemization during the preparation, because (S,S)-3 shows CD of the opposite sign to (R,R)-3 (Figure S4, Supporting Information).
46. Bonadies, J. A.; Maroney, M. J.; Pecoraro, V. L. Inorg. Chem. 1989, 28, 2044-2051.
47. 3 are not equivalent in solution.
48. Ming, L.-J. In Physical Methods in Bioinorganic Chemistry, Spectroscopy and Magnetism; Que, L. , Jr., Ed.; University Science Books: CA, 2000; p 375.
49. (a) Nakatsuji, H. Chem. Phys. Lett. 1978, 59, 362-364.
50. (b) Nakatsuji, H. Chem. Phys. Lett. 1979, 67, 329-333.
51. For example, see: (a) Mizutani, T.; Yagi, S.; Morinaga, T.; Nomura, T.; Takagishi, T.; Kitagawa, S.; Ogoshi, H. J. Am. Chem. Soc. 1999, 121, 754-759.
52. (b) Inai, Y.; Tagawa, K.; Takasu, A.; Hirabayashi, T.; Oshikawa, T.; Yamashita, M. J. Am. Chem. Soc. 2000, 122, 11731-11732.
53. Kurtán, T.; Nesnas, N.; Koehn, F. E.; Li, Y.-Q.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2001, 123, 5974-5982.
54. Kano, K.; Hasegawa, H. J. Am. Chem. Soc. 2001, 123, 10616-10627.
55. (e) Lintuluoto, J. M.; Borovkov, V. V.; Inoue, Y. J. Am. Chem. Soc. 2002, 124, 13676-13677.
56. (f) Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342.
57. (g) Yu, J.; RajanBabu, T. V.; Parquette, J. R. J. Am. Chem. Soc. 2008, 130, 7845-7847.
58. Bell, R. P. The Proton in Chemistry, 2nd ed.; Cornel University Press: Ithaca, NY, 1973.
59. Bjerrum, J.; Schwarzenbach, G.; Sillén, L. G. Stability Constants of Metal-Ion Complexes; Chemical Society: London, 1958.
60. Ballinger, P.; Long, F. A. J. Am. Chem. Soc. 1959, 81, 1050-1053.
61. (a) CrystalClear 1.3.5 SP2; Rigaku and Molecular Structure Corp.: The Woodlands, TX, 2004.
62. (b) Pflugrath, J. W. Acta Crystallogr. 1999, D55, 1718-1725.
63. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122.
64. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997.
65. Sheldrick, G. M. SHELXL-97, Program for Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
66. (a) CrystalStructure 3.8.2: Crystal Structure Analysis Package, version 3.8.2; Rigaku and Rigaku/MSC: The Woodlands, TX, 2007.
67. (b) Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. Crystals, Issue 10; Chemical Crystallography Laboratory: Oxford, U.K., 1996.
68. Flack, H. D. Acta Crystallogr. 1983, A39, 876-881.
69. Frisch, M. J. Gaussian03, revision C.03; Gaussian, Inc.: Wallingford, CT, 2004.
70. Nishiyama, Y.; Kakushou, F.; Sonoda, N. Bull. Chem. Soc. Jpn. 2000, 73, 2779-2782.
71. Larrow, J. F.; Jacobsen, E. N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939-1942.