Supramolecular catalysis at work: Diastereoselective synthesis of a molecular bowl with dynamic inner space

Journal of Organic Chemistry

Volumn 73, Issue 2, 2008, Pages 355-363

  Yan, Zhiqing ^a   McCracken, Troy ^a   Xia, Shijing ^a   Maslak, Veselin ^a   Gallucci, Judith ^a   Hadad, Christopher M ^a   Badjić, Jovica D ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; POSITIVE IONS;

AROMATIC ARMS; DIASTEREOSELECTIVE SYNTHESIS; MOLECULAR BOWL;

SUPRAMOLECULAR CHEMISTRY;

AROMATIC COMPOUND; CATION; COPPER; COPPER COMPLEX; GOLD; NORBORNENE DERIVATIVE; PALLADIUM COMPLEX; SILVER; HEAVY METAL; NORBORNANE DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; BINDING KINETICS; CATALYSIS; COMPLEX FORMATION; CONCENTRATION RESPONSE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ENERGY YIELD; ENTHALPY; ENTROPY; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; CALORIMETRY; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; MACROMOLECULE; STEREOISOMERISM; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

CALORIMETRY; CATALYSIS; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MACROMOLECULAR SUBSTANCES; METALS, HEAVY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NORBORNANES; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; THERMODYNAMICS;

EID: 40949152778     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701538g     Document Type: Article

References (96)

1. (a) Judice, J. K.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2790-2791.
2. (b) Quan, M. L. C.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2754-2755.
3. (c) Cram, D. J.; Blanda, M. T.; Paek, K.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7765-7773.
4. (d) Nakamura, K.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 1853-1854.
5. (e) Houk, K. N.; Nakamura, K.; Sheu, C.; Keating, A. E. Science 1996, 273, 627-629.
6. (f) Sheu, C.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 8056-8070.
7. (g) Raymo, F. M.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 1998, 120, 9318-9322.
8. (h) Ihm, C.; Kim, M.; Ihm, H.; Paek, K. J. Chem. Soc., Perkin Trans. 2 1999, 8, 1569-1575.
9. (i) Chapman, R. G.; Sherman, J. C. J. Am. Chem. Soc. 1999, 121, 1962-1963.
10. (j) Warmuth, R.; Yoon, J. Acc. Chem. Res. 2001, 34, 95-105.
11. (k) Yoon, J.; Warmuth, R. Org. Lett. 2007, 9, 2883-2886.
12. (a) Maslak, V.; Yan, Z.; Xia, S.; Gallucci, J.; Hadad, C. M.; Badjić, J. D. J. Am Chem. Soc. 2006, 128, 5887-5894.
13. (b) Yan, Z.; Xia, S.; Gardlik, M.; Seo, W.; Hadad, C. M.; Badjić, J. D. Org. Lett. 2007, 9, 2301-2304.
14. Yan, Z.; Chang, Y.; Mayo, D.; Xia, S.; Maslak, V.; Badjić, J. D. Org. Lett. 2006, 8, 1697-3700.
15. (a) Cuevas, F.; Di Stefano, S.; Magrans, J. O.; Prados, P.; Mandolini, L.; de Mendoza, J. Chem. Eur. J. 2000, 6, 3228-3234.
16. (b) Davis, A. V.; Yeh, R. M.; Raymond, K. N. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4793-4796.
17. (c) Zyryanov, G. V.; Rudkevich, D. M. Org. Lett. 2003, 5, 1253-1256.
18. (d) Gianneschi, N. C.; Bertin, P. A.; Nguyen SonBinh T.; Mirkin, C. A.; Zakharov, L. N.; Rheingold, A. L. J. Am. Chem. Soc. 2003, 125, 10508-10509.
19. (e) Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2004, 43, 6748-6751.
20. (f) Yoshizawa, M.; Miyagi, S.; Kawano, M.; Ishiguro, K.; Fujita, M. J. Am. Chem. Soc. 2004, 126, 9172-9173.
21. (g) Palmer, L. C.; Rebek, J., Jr. Org. Biomol. Chem. 2004, 2, 3051-3059.
22. (h) Kaanumalle, L. S.; Gibb, C. L. D.; Gibb Bruce, C.; Ramamurthy, V. J. Am. Chem. Soc. 2004, 126, 14366-14367.
23. (i) Hooley, R. J.; Rebek, J., Jr. J. Am. Chem. Soc. 2005, 127, 11904-11905.
24. (j) Luetzen, A. Angew. Chem., Int. Ed. 2005, 44, 1000-1002.
25. (k) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870.
26. (l) Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251-254.
27. (a) Siegel, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1721-1723.
28. (b) Frank, N. L.; Baldridge, K. K.; Gantzel, P.; Siegel, J. S. Tetrahedron Lett. 1995, 36, 4389-4392.
29. (c) Buergi, H-B.; Baldridge, K. K.; Hardcastle, K.; Frank, N. L.; Gantzel, P.; Siegel, J. S.; Ziller, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1454-1456.
30. (a) Gassman, P. G.; Gennick, I. J. Am. Chem. Soc. 1980, 102, 6863-6864.
31. (b) Durr, R.; De Lucchi, O.; Cossu, S.; Lucchini, V. Chem. Commun. 1996, 2, 2447-2448.
32. (c) Durr, R.; Cossu, S.; Lucchini, V.; De Lucchi, O. Angew. Chem., Int. Ed. Engl. 1997, 36, 2805-2807.
33. (d) Sakurai, H.; Daiko, T.; Hirao, T. Science 2003, 301, 1878-1882.
34. (a) Zonta, C.; Cossu, S.; Peluso, P.; De Lucchi, O. Tetrahedron Lett. 1999, 40, 8185-8188.
35. (b) Cossu, S.; De Lucchi, O.; Paulon, A.; Peluso, P.; Zonta, C. Tetrahedron Lett. 2001, 42, 3515-3518.
36. (c) Peluso, P.; De Lucchi, O.; Cossu, S. Eur. J. Org. Chem. 2002, 23, 4032-4036.
37. (a) Fabris, F.; De Martin, A.; De Lucchi, O. Tetrahedron Lett. 1999, 40, 9121-9124.
38. (b) Paulon, An.; Cossu, S.; De Lucchi, O.; Zonta, C. Chem. Commun. 2000, 19, 1837-1838.
39. (c) Cossu, S.; Cimenti, C.; Peluso, P.; Paulon, A.; De Lucchi, O. Angew. Chem., Int. Ed. 2001, 40, 4086-4089.
40. (d) Borsato, G.; De Lucchi, O.; Fabris, F.; Groppo, L.; Lucchini, V.; Zambon, A. J. Org. Chem. 2002, 67, 7894-7897.
41. (e) Borsato, G.; De Lucchi, O.; Fabris, F.; Lucchini, V.; Pasqualotti, M.; Zambon, A. Tetrahedron Lett. 2002, 44, 561-563.
42. (f) Fabris, F.; Bellotto, L.; De Lucchi, O. Tetrahedron Lett. 2003, 44, 1211-1213.
43. (g) Zonta, C.; Fabris, F.; De Lucchi, O. Org. Lett. 2005, 7, 1003-1006.
44. (a) Liebeskind, L. S.; Fengi, R. W. J. Org. Chem. 1990, 55, 5359-5364.
45. (b) Han, X.; Stolz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600-7605.
46. (c) Casado, A. L.; Espinet, P. Organometallics 2003, 22, 1305-1309.
47. (d) Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132-1136.
48. Newman, M. S.; Addor, R. W. J. Am. Chem. Soc. 1955, 77, 3789-3793.
49. Kobayashi, T.; Kobayashi, S. Molecules 2000, 5, 1062-1067.
50. (a) Colter, A.; Friedrich, E. C.; Holness, N. J.; Winstein, S. J. Am. Chem. Soc. 1965, 87, 378-379.
51. (b) Walling, C. Acc. Chem. Res. 1983, 16, 448-454.
52. (c) Tutar, A.; Taskesenligil, Y.; Cakmak, O.; Abbasoglu, R.; Balci, M. J. Org. Chem. 1996, 61, 8297-8300.
53. Kobayashi, T.; Miki, K. Bull. Chem. Soc. Jpn. 1998, 71, 1443-1449.
54. For recent reviews explaining the principles of template-directed synthesis see: (a) Jager, R.; Vogtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930-944.
55. (b) Hubin, T. J.; Kolchinski, A. G.; Vance, A. L.; Busch, D. H. Adv. Supramol. Chem. 1999, 5, 237-357.
56. (c) Arico, F.; Badjić, J. D.; Flood, A.; Leung, K.; Liu, Y.; Stoddart, J. F. Top. Curr. Chem. 2005, 249, 203-261.
57. (d) Lankshear, M. D.; Beer, P. D. Coord. Chem. Rev. 2006, 250, 3142-3160.
58. See the Supporting Information for more details.
59. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
60. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons, Inc.: New York, 1997; Vol. 50.
61. (c) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
62. Wilcox, C. Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H-J., Durr, H., Eds.; Wiley-VCH: Weinheim, Germany, 1991; pp 123-143.
63. (a) Connors, K. A. Binding Constants, The Measurement of Molecular Complex Stability; Wiley-Interscience: New York, 1987; pp 24-28.
64. (b) Blanda, M. T.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1989, 54, 4626-4636.
65. (a) Wilcox, C. F.; Leung, C. J. J. Am. Chem. Soc. 1968, 90, 336-341.
66. (b) Cole, T. W., Jr.; Mayers, C. J.; Stock, L. M. J. Am. Chem. Soc. 1974, 96, 4555-4557.
67. (c) Grubbs, E. J.; Wang, C.; Deardurff, L. A. J. Org. Chem. 1984, 49, 4080-4082.
68. Ruloff, R.; Seelbach, U. T.; Merbach, A. E.; Klarner, F.-G. J. Phys. Org. Chem. 2002, 15, 189-196.
69. (a) Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
70. (b) Becke, A. D. Phys. Rev. A 1998, 38, 3098.
71. For an additional role of Ag(I) in improving Stille couplings see: Gronowitz, S.; Messmer, A.; Timari, G. J. Heterocycl. Chem. 1992, 29, 1049-.
72. 30
73. DENZO: Otwinowski, Z.; Minor, W. Methods Enzymology; Vol. 276, Macromolecular Crystallography, Part A; Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press: New York, 1997; pp 307-326.
74. Sheldrick, G. M. SHELXS-97; Universitat Gottingen: Gottingen, Germany, 1997.
75. Sheldrick, G. M. SHELXL-97; Universitat Gottingen: Gottingen, Germany, 1997.
76. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
77. Sluis, P. V. D.; Spek, A. L. Acta Crystallogr. 1990, A46, 194.
78. Spek, A. L. Acta Crystallogr. 1990, A46, C34.
79. International Tables for Crystallography; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; Vol. C.
80. (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
81. (b) Cockroft, S. L.; Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Am. Chem. Soc. 2005, 127, 8594.
82. syn was calculated following Rebek's protocol. See: Mecossi, S.; Rebek, J., Jr. Chem. Eur. J. 1998, 37, 3303.
83. Jeffrey, A. G. An Introduction to Hydrogen Bonding; Oxford University Press, Inc.: New York, 1997; pp 11 and 12.
84. For recent studies employing the BP86 functional in investigating organometallic systems, see: (a) Wang, F.; Li, L. M. J. Comput. Chem. 2004, 25 (5), 669.
85. (b) Silva, V. D.; Dias, R. P.; Rocha, W. R. Chem. Phys. Lett. 2007, 439, 69.
86. (c) Nakamura, A.; Ohshima, T.; Mashima, K. J. Organomet. Chem. 2005, 690, 4373.
87. For a recent comparison of DFT methods for organometallic systems, see: Furche, F.; Perdew, J. P. J. Chem. Phys. 2006, 124, 044013.
88. Eichkorn, K.; Treutier, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 242, 652.
89. Eichkorn, K.; Weigend, F.; Treutier, O.; Ahlrichs, R. Theor. Chem. Acc. 1997, 97, 119.
90. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
91. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
92. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kolmel, C. Chem. Phys. Lett. 1989, 162, 165.
93. Häser, M.; Ahlrichs, R. J. Comput. Chem. 1989, 10, 104.
94. Von Arnim, M.; Ahlrichs, R. J. Comput. Chem. 1998, 19, 1746.
95. Deglmann, P.; Furche, F.; Ahlrichs, R. Chem. Phys. Lett. 2002, 362, 511.
96. The Turbomole basis set library is available via ftp from ftp://ftp.chemie.uni-karlsruhe.de/pub/basen.