One-pot synthesis of helical aromatics: Stereoselectivity, stability against racemization, and assignment of absolute configuration assisted by experimental and theoretical circular dichroism

Journal of Organic Chemistry

Volumn 69, Issue 23, 2004, Pages 7794-7801

  Watanabe, Masashi ^a   Suzuki, Hiroshi ^a   Tanaka, Yasutaka ^a   Ishida, Toshimasa ^b   Oshikawa, Tatsuo ^c   Tori i, Akiyoshi ^d  

^a SHIZUOKA UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^c NUMAZU COLLEGE OF TECHNOLOGY   (Japan)

^d SAGA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CONDENSATION; MICROWAVES; SOLVENTS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY; HELICAL AROMATICS; LEWIS ACID; MICROWAVE IRRADIATION;

AROMATIC COMPOUNDS;

13,14 DIALKYLBENZO[B,J][4,7]PHENANTHROLINE; 2 METHYLGLUTARIC ACID; AROMATIC COMPOUND; CARBOXYLIC ACID; GLUTARIC ACID DERIVATIVE; LEWIS ACID; N,N' 4 PHENYLENEDIAMINE; PHENANTHROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DENSITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICROWAVE IRRADIATION; POLYMERIZATION; RACEMIZATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 8644288169     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048858k     Document Type: Article

References (58)

1. 5,8-Diazapentaphene rings (dibenzo[b,j][4,7]-phenanthroline) have been known since the 1950s; see: (a) Badger, G. M.; Pettit, R. J. Chem. Soc. 1952, 1874. (b) Hellwinkel, D.; Ittemann, P. Liebigs Ann. Chem. 1985, 1501.
2. 5,8-Diazapentaphene rings (dibenzo[b,j][4,7]-phenanthroline) have been known since the 1950s; see: (a) Badger, G. M.; Pettit, R. J. Chem. Soc. 1952, 1874. (b) Hellwinkel, D.; Ittemann, P. Liebigs Ann. Chem. 1985, 1501.
3. For a review of aromatic helical molecules, see: (a) Wynberg, H. Acc. Chem. Res. 1971, 4, 65. (b) Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63. (d) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1.
4. For a review of aromatic helical molecules, see: (a) Wynberg, H. Acc. Chem. Res. 1971, 4, 65. (b) Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63. (d) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1.
5. For a review of aromatic helical molecules, see: (a) Wynberg, H. Acc. Chem. Res. 1971, 4, 65. (b) Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63. (d) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1.
6. For a review of aromatic helical molecules, see: (a) Wynberg, H. Acc. Chem. Res. 1971, 4, 65. (b) Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63. (d) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1.
7. For a review of chiroptical properties, see: (e) Grimme, S.; Harren, J.; Sobanski, A.; Vögtle, F. Eur. J. Org. Chem., 1998, 1491.
8. (a) Murguly, E.; McDonald, R.; Branda, N. R. Org. Lett. 2000, 2, 3169.
9. (b) Sato, I.; Yamashima, R.; Kadowaki, K.; Yamamoto, J.; Shibata, T.; Soai, K. Angew. Chem., Int. Ed. 2001, 40, 1096.
10. (c) Reetz, M. T.; Sostman, S. Tetrahedron 2001, 57, 2515.
11. (d) Schmuck, C. Angew. Chem., Int. Ed. 2003, 42, 2448.
12. (e) Urbano, A. Angew. Chem., Int. Ed. 2003, 42, 3986.
13. (a) Katz, T. J. Angew. Chem., Int. Ed. 2000, 39, 1921.
14. (b) Verbiest, T.; Sioncke, S.; Persoons, A.; Vyklicky, L.; Katz, T. J. Angew. Chem., Int. Ed. 2002, 41, 3882.
15. (a) Tanaka, Y.; Sekita, A.; Suzuki, H.; Yamashita, M.; Oshikawa, T.; Yonemitsu, T.; Torii, A. J. Chem Soc., Perkin Trans. 1 1998, 2471.
16. (b) Tanaka, Y.; Sekita, A.; Suzuki, H.; Torii, A. U.S. Patent 5973151, 1999.
17. For the reaction mechanism for 9-substituted acridines from diphenylamine and carboxylic acid, see: (a) Tsuge, O.; Nishinohara, M.; Tashiro, M. Bull. Chem. Soc. Jpn. 1963, 36, 1477. (b) Bernthsen, A. Justus Liebigs Ann. Chem. 1884, 1, 224.
18. For the reaction mechanism for 9-substituted acridines from diphenylamine and carboxylic acid, see: (a) Tsuge, O.; Nishinohara, M.; Tashiro, M. Bull. Chem. Soc. Jpn. 1963, 36, 1477. (b) Bernthsen, A. Justus Liebigs Ann. Chem. 1884, 1, 224.
19. 1H NMR spectra of 8c and 8c′ are shown in Supporting Information.
20. N1,N4-Diphenyl-1,4-benzenendiamine and N1-[4-methyl(phenyl)- carboxamidophenyl]-N1-phenylacetamide are in the IUPAC nomenclature of 2 and 6a′.
21. z component; see also Experimental Section.
22. Experimental as well as theoretical CD spectra of 1a and 4a have shapes identical to those of 1b and 4b, respectively, which are not unexpected from close structural similarities.
23. s-symmetric conformation in the transition state has been proposed by molecular orbital methods of AM1, MNDO, and PM3 to account for racemization of helicenes; see: Janke, R. H.; Haufe, G.; Würthwein, E.-U.; Borkent, J. H. J. Am. Chem. Soc. 1996, 118, 6031.
24. (a) Goedicke, C.; Stegemeyer, H.; Tetrahedron Lett. 1970, 11, 937.
25. (b) Carreño, M. C.; Carcía-Cerrada, S.; Urbano, A. J. Am. Chem. Soc. 2001, 123, 7929.
26. 3 carbon at the 13 position, which was derived from the chiral carbon in 3f, and (M) denotes the helicity of the conjugated aromatic plane.
27. For a recent review of microwave-assisted organic synthesis, see: (a) Microwave-Enhanced Chemistry; Kingston, H. M., Haswell, S. J., Eds.; American Chemical Society: Washington, DC, 1997, (b) Microwaves in Organic Synthesis; Loupy, A, Eds.; Wiley-VCH: Weinheim, 2002. (c) Caddick, S. Tetrahedron 1995, 51, 10403. Loupy, A.; Perreux, L.; Liagre, M.; Burle, K.; Moneuse, M. Pure Appl. Chem. 2001, 73, 161. (d) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (e) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225. (f) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5662.
28. For a recent review of microwave-assisted organic synthesis, see: (a) Microwave-Enhanced Chemistry; Kingston, H. M., Haswell, S. J., Eds.; American Chemical Society: Washington, DC, 1997, (b) Microwaves in Organic Synthesis; Loupy, A, Eds.; Wiley-VCH: Weinheim, 2002. (c) Caddick, S. Tetrahedron 1995, 51, 10403. Loupy, A.; Perreux, L.; Liagre, M.; Burle, K.; Moneuse, M. Pure Appl. Chem. 2001, 73, 161. (d) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (e) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225. (f) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5662.
29. For a recent review of microwave-assisted organic synthesis, see: (a) Microwave-Enhanced Chemistry; Kingston, H. M., Haswell, S. J., Eds.; American Chemical Society: Washington, DC, 1997, (b) Microwaves in Organic Synthesis; Loupy, A, Eds.; Wiley-VCH: Weinheim, 2002. (c) Caddick, S. Tetrahedron 1995, 51, 10403. Loupy, A.; Perreux, L.; Liagre, M.; Burle, K.; Moneuse, M. Pure Appl. Chem. 2001, 73, 161. (d) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (e) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225. (f) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5662.
30. For a recent review of microwave-assisted organic synthesis, see: (a) Microwave-Enhanced Chemistry; Kingston, H. M., Haswell, S. J., Eds.; American Chemical Society: Washington, DC, 1997, (b) Microwaves in Organic Synthesis; Loupy, A, Eds.; Wiley-VCH: Weinheim, 2002. (c) Caddick, S. Tetrahedron 1995, 51, 10403. Loupy, A.; Perreux, L.; Liagre, M.; Burle, K.; Moneuse, M. Pure Appl. Chem. 2001, 73, 161. (d) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (e) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225. (f) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5662.
31. For a recent review of microwave-assisted organic synthesis, see: (a) Microwave-Enhanced Chemistry; Kingston, H. M., Haswell, S. J., Eds.; American Chemical Society: Washington, DC, 1997, (b) Microwaves in Organic Synthesis; Loupy, A, Eds.; Wiley-VCH: Weinheim, 2002. (c) Caddick, S. Tetrahedron 1995, 51, 10403. Loupy, A.; Perreux, L.; Liagre, M.; Burle, K.; Moneuse, M. Pure Appl. Chem. 2001, 73, 161. (d) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (e) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225. (f) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5662.
32. For a recent review of microwave-assisted organic synthesis, see: (a) Microwave-Enhanced Chemistry; Kingston, H. M., Haswell, S. J., Eds.; American Chemical Society: Washington, DC, 1997, (b) Microwaves in Organic Synthesis; Loupy, A, Eds.; Wiley-VCH: Weinheim, 2002. (c) Caddick, S. Tetrahedron 1995, 51, 10403. Loupy, A.; Perreux, L.; Liagre, M.; Burle, K.; Moneuse, M. Pure Appl. Chem. 2001, 73, 161. (d) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (e) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225. (f) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5662.
33. For a recent review of microwave-assisted organic synthesis, see: (a) Microwave-Enhanced Chemistry; Kingston, H. M., Haswell, S. J., Eds.; American Chemical Society: Washington, DC, 1997, (b) Microwaves in Organic Synthesis; Loupy, A, Eds.; Wiley-VCH: Weinheim, 2002. (c) Caddick, S. Tetrahedron 1995, 51, 10403. Loupy, A.; Perreux, L.; Liagre, M.; Burle, K.; Moneuse, M. Pure Appl. Chem. 2001, 73, 161. (d) Varma, R. S. Pure Appl. Chem. 2001, 73, 193. (e) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225. (f) Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 5662.
34. 9-Substituted acridines were recently synthesized by microwave irradiation; see: (a) Veveková, E.; M. Nosková, M.; Toma, S. Synth. Commun. 2002, 32, 729. (b) Koshima, H.; Kutsunai, K. Heterocycles 2002, 57, 1299. (c) Seijas, J. A.; Vazquez-Tato, M. P.; Martinez, M. M.; Rodriguez-Parga, J. Green Chem. 2002, 4, 390.
35. 9-Substituted acridines were recently synthesized by microwave irradiation; see: (a) Veveková, E.; M. Nosková, M.; Toma, S. Synth. Commun. 2002, 32, 729. (b) Koshima, H.; Kutsunai, K. Heterocycles 2002, 57, 1299. (c) Seijas, J. A.; Vazquez-Tato, M. P.; Martinez, M. M.; Rodriguez-Parga, J. Green Chem. 2002, 4, 390.
36. 9-Substituted acridines were recently synthesized by microwave irradiation; see: (a) Veveková, E.; M. Nosková, M.; Toma, S. Synth. Commun. 2002, 32, 729. (b) Koshima, H.; Kutsunai, K. Heterocycles 2002, 57, 1299. (c) Seijas, J. A.; Vazquez-Tato, M. P.; Martinez, M. M.; Rodriguez-Parga, J. Green Chem. 2002, 4, 390.
37. (a) Harada, N.; Nakanishi, K. In Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
38. (b) Berova, N.; Nakanishi, K. In Circular Dichroism, Principles and Applications; Nakanishi, K.; Berova, N.; Woody, R., Eds.; VHC: New York, 1994.
39. (c) Rodger, A.; Nordén, B. In Circular Dichroism and Linear Dichroism; Oxford, Oxford, New York, 1997.
40. Provisional assignment of absolute configuration of 4a in our previous communication (ref 4) was incorrect. We previously misjudged the direction of screwness between two long axes of the chromophores. For CD spectra of molecules possessing identical orientation of two chromophores to 4a, see: (a) Imajo, S.; Nakamura, A.; Shingu, K.; Kato, A ; Nakagawa, M. J. Chem. Soc., Chem. Commun. 1979, 867. (b) Imajo, S.; Kato, A.; Shingu, K.; Kuritani, H. Tetrahedron Lett. 1981, 22, 2179. (c) Shingu, K.; Imajo, S.; Kato, A.; Kuritani, H. J. Am. Chem. Soc. 1982, 104, 4272.
41. Provisional assignment of absolute configuration of 4a in our previous communication (ref 4) was incorrect. We previously misjudged the direction of screwness between two long axes of the chromophores. For CD spectra of molecules possessing identical orientation of two chromophores to 4a, see: (a) Imajo, S.; Nakamura, A.; Shingu, K.; Kato, A ; Nakagawa, M. J. Chem. Soc., Chem. Commun. 1979, 867. (b) Imajo, S.; Kato, A.; Shingu, K.; Kuritani, H. Tetrahedron Lett. 1981, 22, 2179. (c) Shingu, K.; Imajo, S.; Kato, A.; Kuritani, H. J. Am. Chem. Soc. 1982, 104, 4272.
42. Provisional assignment of absolute configuration of 4a in our previous communication (ref 4) was incorrect. We previously misjudged the direction of screwness between two long axes of the chromophores. For CD spectra of molecules possessing identical orientation of two chromophores to 4a, see: (a) Imajo, S.; Nakamura, A.; Shingu, K.; Kato, A ; Nakagawa, M. J. Chem. Soc., Chem. Commun. 1979, 867. (b) Imajo, S.; Kato, A.; Shingu, K.; Kuritani, H. Tetrahedron Lett. 1981, 22, 2179. (c) Shingu, K.; Imajo, S.; Kato, A.; Kuritani, H. J. Am. Chem. Soc. 1982, 104, 4272.
43. For a review of the limitations of the CD exciton chirality method, see: Superchi, S.; Giorgio, E.; Rosini, C. Chirality 2004, 16, 422.
44. (a) Grimme, S.; Harren, J.; Sobanski, A.; Vögtle, F. Eur. J. Org. Chem. 1988, 53, 1.
45. (b) Furche, F.; Ahlrichs, R.; Wachsmann, C.; Weber, E.; Sobanski, A.; Vögtle, F. Grimme, S. J. Am. Chem. Soc. 2000, 122, 1717.
46. 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.; 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 B.01; Gaussian, Inc.: Pittsburgh, PA, 2003.
47. Difference in wavelength and absorption coefficient between theoretical and experimental CD and absorption spectra was partly rationalized by solvent effects and the systematic underestimation of higher excitation energies in TDDFT; see ref 18 and: Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1986, 256, 454.
48. -1 at 27°C, respectively; see: (a) Martin, R. H.; Marchant, M. J. Tetrahedron 1974, 30, 347. (b) Janke, R. H.; Haufe, G.; Würthwein, E.-U.; Borkent, H. J. Am. Chem. Soc. 1996, 118, 6031. (c) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110.
49. -1 at 27°C, respectively; see: (a) Martin, R. H.; Marchant, M. J. Tetrahedron 1974, 30, 347. (b) Janke, R. H.; Haufe, G.; Würthwein, E.-U.; Borkent, H. J. Am. Chem. Soc. 1996, 118, 6031. (c) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110.
50. -1 at 27°C, respectively; see: (a) Martin, R. H.; Marchant, M. J. Tetrahedron 1974, 30, 347. (b) Janke, R. H.; Haufe, G.; Würthwein, E.-U.; Borkent, H. J. Am. Chem. Soc. 1996, 118, 6031. (c) Meier, H.; Schwertel, M.; Schollmeyer, D. Angew. Chem., Int. Ed. 1998, 37, 2110.
51. Ni-i, T.; Matsumura, T.; Oka, T. Kagaku to Kyouiku 1993, 41, 278.
52. CrystalClear; Rigaku Corporation: 1999. CrystalClear Software User's Guide; Molecular Structure Corporation: 2000. Pflugrath, J. W. Acta Crystallogr. 1999, D55, 1718-1725.
53. CrystalClear; Rigaku Corporation: 1999. CrystalClear Software User's Guide; Molecular Structure Corporation: 2000. Pflugrath, J. W. Acta Crystallogr. 1999, D55, 1718-1725.
54. CrystalClear; Rigaku Corporation: 1999. CrystalClear Software User's Guide; Molecular Structure Corporation: 2000. Pflugrath, J. W. Acta Crystallogr. 1999, D55, 1718-1725.
55. (a) CrystalStructure 3.6.0: Crystal Structure Analysis Package; Rigaku and Rigaku/MSC: The Woodlands, TX, 2004.
56. (b) Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. CTYSTALS Issue 10; Chemical Crystallography Laboratory: Oxford, UK, 1996.
57. Sheldrick, G. M. SHELX97; 1997.
58. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M.; The DIRDIF-99 Program System, Technical Report of the Crystallography Laboratory; University of Nijmegen: Nijmegen, The Netherlands, 1999.