Synthesis of, and structural assignments to the stereoisomers of bis (2,2′)- and tris (2,2′,2″)-tetrahydrofurans: Conformational features and ionic binding capacities of these gateway polycyclic networks

Journal of Organic Chemistry

Volumn 72, Issue 16, 2007, Pages 6215-6223

  Adaligil, Emel ^a   Davis, Barry D ^b   Hilmey, David G ^c   Shen, Young ^a   Spruell, Jason M ^a   Brodbelt, Jennifer S ^b   Houk, K N ^a   Paquette, Leo A ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^c OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALDEHYDES; ALKALI METALS; ENANTIOMERS; SYNTHESIS (CHEMICAL);

DECARBONYLATION; IONIC BINDING; TETRAHYDROFURANS; THF;

ADDITION REACTIONS;

ACETONE; ALKALI METAL; LITHIUM ION; POTASSIUM ION; RHODIUM; SODIUM ION; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; ELECTROSPRAY MASS SPECTROMETRY; ENERGY; GAS; STEREOISOMERISM; SYNTHESIS;

EID: 34547614498     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0708238     Document Type: Article

References (81)

1. (a) Zefirov, N. S. Tetrahedron 1977, 33, 3193.
2. (b) Zefirov, N. S.; Samoshin, V. V.; Subbotin, O. A.; Baranenkov, V. I.; Wolfe, S. Tetrahedron 1978, 34, 2953.
3. Van-Catledge, F. A. J. Am. Chem. Soc 1974, 96, 5693.
4. (a) Wolfe, S.; Rauk, A.; Tel, L. M.; Csizmadia, I. G. J. Chem. Soc. B 1971, 136.
5. (b) Wolfe, S.; Tel, L. M.; Haines, W. J.; Robb, M. A.; Csizmadia, I. G. J. Am. Chem. Soc. 1973, 95, 4863.
6. (c) Wolfe, S. Acc. Chem. Res. 1972, 5, 102.
7. (a) Phillips, L.; Wray, V. J. Chem. Soc. Chem. Commun. 1973, 90.
8. (b) Juaristi, E.; Antunez, S. Tetrahedron 1992, 48, 5941.
9. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley: New York, 1994; pp 606-615.
10. (a) Gokel, G. Crown Ethers and Cryptands; The Royal Society of Chemistry: Cambridge, England, 1991.
11. (b) Cooper, S. R., Ed. Crown Compounds: Toward Future Applications; VCH Publishers: New York, 1992.
12. (c) Vögtle, F. Supramolecular Chemistry; John Wiley and Sons: Chichester, England, 1991.
13. (d) Inoue, Y.; Gokel, G. W. Cation Binding by Macrocycles; Marcel Dekker: New York, 1990.
14. (e) Westley, W. J., Ed. Polyether Antibiotics; Marcel Dekker: New York, 1983; Vols. I and II.
15. (f) Dobler, M. Ionophores and Their Structures; Wiley-Inter-science: New York, 1981.
16. (g) Izatt, R. M.; Christensen, J. J. Synthetic Multidentate Macrocyclic Compounds; Academic Press: New York, 1978.
17. (a) Koert, U.; Stein, M.; Harms, K. Angew. Chem., Int. Ed. Eng. 1994, 33, 1180.
18. st Century; Keinan, I., Schechter, I., Eds.; Wiley-VCH: Weinheim, 2001; 37-53.
19. Matsuura, H.; Miyauchi, N.; Murata, H.; Sakakibara, M. Bull. Soc. Chem. Jpn. 1979, 52, 344.
20. (a) Ohsaku, M.; Imamura, A. Macromolecules 1978, 11, 970.
21. (b) Abe, A.; Mark, J. E. J. Am. Chem. Soc. 1976, 98, 6468.
22. (c) Eliel, E. L. Acc. Chem. Res. 1970, 3, 1.
23. (a) Berthelot, M.; Besseau, F.; Laurence, C. Eur. J. Org. Chem. 1998, 925.
24. (b) Catalan, J.; Gomez, J.; Couto, A.; Laynez, J. J. Am. Chem. Soc. 1990, 112, 1678.
25. (c) Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J.; Laurence, C.; Berthelot, M. Tetrahedron Lett. 1989, 30, 2571.
26. (d) Laurence, C.; Nicolet, P.; Herbert, M. J. Chem. Soc., Perkin Trans. 2 1986, 1081.
27. Bordeje, M. C.; Mo, O.; Yanez, M.; Herreros, M.; Abboud, J. L. M. J. Am. Chem. Soc. 1993, 115, 7389.
28. (a) Pines, E.; Fleming, G. R. Isr. J. Chem. 1993, 33, 179.
29. (b) Krygowski, T. M.; Radomski, J. P.; Rzeszowiak, A.; Wrona, P. K.; Reichardt, C. Tetrahedron 1981, 37, 119.
30. (c) Westera, G.; Blomberg, C.; Bickelhaupt, F. Organomet. Chem. 1978, 155, C55.
31. (d) Arnett, E. M.; Mitchell, E. J.; Murty, T. S. S. R. J. Am. Chem. Soc. 1974, 96, 3875.
32. (e) Lee, D. G.; Cameron, R. Can. J. Chem. 1972, 50, 445.
33. (a) Paquette, L. A.; Tae, J.; Hickey, E. R.; Trego, W. E.; Rogers, R. D. J. Org. Chem. 2000, 65, 9160.
34. (b) See also: Paquette, L. A.; Ra, C. S.; Gallucci, J. C.; Kang, H.-J.; Ohmori, N.; Arrington, M. P.; David, W.; Brodbelt, J. S. J. Org. Chem. 2001, 66, 8629.
35. Anderson, J. E.; Angyal, S. J.; Craig, D. C. Carbohydr. Res. 1995, 272, 141.
36. Paquette, L. A.; Tae, J.; Branan, B. M.; Bolin, D. G.; Eisenberg, S. W. E. J. Org. Chem. 2000, 65, 9172.
37. See also: Paquette, L. A.; Stepanian, M.; Branan, B. M.; Edmon son, S. D.; Bauer, C. B.; Rogers, R. D. J. Am. Chem. Soc. 1996, 118, 4504.
38. Anderson, J. E. J. Chem. Soc. Perkin Trans. 2 1993, 441.
39. (a) Rablen, P. R.; Paquette, L. A.; Borden, W. T. J. Org. Chem. 2000, 65, 9180.
40. (b) Hay, B. P.; Oliferenko, A. A.; Uddin, J.; Zhang, C.; Firman, T. K. J. Am. Chem. Soc. 2005, 127, 17043.
41. (a) Reichstein, T. A.; Grüssner, H.; Zschokke, H. Helv. Chim. Acta 1932, 15, 1066.
42. (b) Kondo, H.; Suzuki, H.; Takeda, K. J. Pharm Soc. Jpn. 1935, 55, 142.
43. (c) Fieser, L. F.; Fry, E. M.; Jones, R. N. J. Am. Chem. Soc 1939, 61, 1849.
44. (d) Shima, K.; Tsutsumi, S. Bull. Chem. Soc. Jpn. 1963, 36, 121.
45. (e) Micovic, V. M.; Stojcic, S.; Mladenovic, S.; Stefanovic, M. Tetrahedron Lett. 1965, 21, 1559.
46. (f) Van Tamelen, E. E.; Schwartz, J.; Brauman, J. I. J. Am. Chem. Soc. 1970, 92, 5798.
47. (g) Sakakibara, T.; Haraguchi, K. Bull. Chem. Soc. Jpn 1980, 53, 279.
48. (h) Yanagida, S.; Azuma, T.; Kawakani, H.; Kizumoto, H.; Sakuraï, H. J. Chem. Soc., Chem. Commun. 1984, 1, 21.
49. (i) Yanagida, S.; Azuma, T.; Midori, Y.; Pac, C.; Sakurai, H. J. Chem. Soc., Perkin Trans. 2 1985, 1487.
50. (j) Kharrat, A.; Gardrat C.; Maillard, B. Can. J. Chem. 1984, 62, 2385.
51. (k) Bourgeois, M. J.; Maillard, B.; Montaudon, E. Tetrahedron 1986, 42, 5309.
52. (l) Zeug, N.; Bücheler J.; Kisch, H. J. Am. Chem. Soc. 1985, 107, 1459.
53. (m) Shine, H. J.; Soroka, M. Tetrahedron 1986, 42, 6111.
54. (n) Crabtree, H.; Brown, S. H. J. Am. Chem. Soc. 1989, 111, 2946.
55. (o) Gevorgyan, V.; Gavars, M.; Liepins, E.; Priede, E.; Lukevics, E. J. Organomet. Chem. 1990, 393, 333.
56. (p) Jung, J. C.; Choi, H. C.; Kim, Y. H. Tetrahedron Lett. 1993, 34, 3581.
57. (q) Murai, A.; Fujiwara, K.; Hayashi, N. Tetrahedron 1997, 53, 12425.
58. (r) Negele, S.; Wieser K.; Severin, T. J. Org. Chem. 1998, 63, 1138.
59. (s) Kelly, D. R.; Nally, J. Tetrahedron Lett. 1999, 40, 2209.
60. Alexakis, A.; Tomassini, A.; Leconte, S. Tetrahedron 2004, 60, 9479.
61. Paquette, L. A.; Hilmey, D. G.; Gallucci, J. C. Org. Lett. 2006, 8, 2635.
62. Calter, M. A.; Zhu, C.; Lachicotte, R. J. Org. Lett. 2002, 4, 209.
63. Cahiez, G.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1978, 3013.
64. (a) Negri, J. T.; Rogers, R. D.; Paquette, L. A. J. Am. Chem. Soc. 1991, 113, 5073.
65. (b) Paquette, L. A.; Negri, J. T.; Rogers, R. D. J. Org. Chem. 1992, 57, 3947.
66. (c) Paquette, L. A.; Stepanian, M.; Mallavadhani, U. V.; Cutarelli, T. D.; Lowinger, T. B.; Klemeyer, H. J. J. Org. Chem. 1996, 61, 7492.
67. For example: Paquette, L. A.; Wiedeman, P. E.; Bulman-Page, P. C. J. Org. Chem. 1988, 53, 1441.
68. Koenig, K. E.; Lein, G. M.; Stuckler, P.; Kaneda, T.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3553.
69. Hilmey, D. G. Ph.D. Dissertation, The Ohio State University, 2006.
70. Blair, S.; Kempen, E.; Brodbelt, J. S. J. Am. Soc. Mass Spectrom. 1998, 9, 1049.
71. Wolfe, S. Accounts Chem. Res. 1972, 5, 102.
72. Lowe, J. P. Prog. Phys. Org. Chem. 1968, 6, 1.
73. (a) Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 1994, 116, 3892.
74. (b) Guvench, O.; MacKerrell, A. D. J. Phys. Chem. A 2006, 110, 9934.
75. (a) Petterson, K. A.; Stein, R. S.; Drake, M. D.; Roberts, J. D. Magn. Reson. Chem. 2005, 43, 225.
76. (b) Bakó, I.; Grósz, T.; Palinkas, G.; Bellissent-Funel, M. C. J. Chem. Phys. 2003, 118, 3215.
77. Tsuzuki, S.; Uchimaru, T.; Tanabe, K.; Hirano, T. J. Phys. Chem. 1993, 97, 1346.
78. Houk, K. N.; Eksterowicz, J. E.; Wu, Y.-D.; Fuglesang, C. D.; Mitchell, D. B. J. Am. Chem. Soc. 1993, 115, 4170.
79. Saunders, M.; Houk, K. N.; Wu, Y. D.; Still, W. C.; Lipton, M.; Chang, G.; Guida, W. C.; J. Am. Chem. Soc. 1990, 112, 1419.
80. Halgren, T. A. J. Comp. Chem. 1999, 20, 730.
81. RHF/6-31G(d): Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.