Axial chirality induction in flexible biphenols by hydrogen bonding and steric interactions

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1991-1994

  Mizutani, Tadashi ^a   Takagi, Hideki ^a   Hara, Osamu ^a   Horiguchi, Takuya ^a   Ogoshi, Hisanobu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; DRUG SYNTHESIS; HYDROGEN BOND;

EID: 0031575780     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00256-6     Document Type: Article

References (29)

1. 1. Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590.
2. 2. (a) Dobashi, Y.; Dobashi, A.; Ochiai, H.; Hara, S. J. Am. Chem. Soc. 1990, 112, 6121-6123.
3. (b) Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1994, 116, 4495-4496.
4. 3. Examples for recognition-triggered dynamic processes, see (a) Beer, P. D.; Rothin, A. S. J. Chem. Soc., Chem. Commun. 1988, 52-54.
5. (b) Ebmeyer, F.; Rebek, J. Jr. Angew. Chem. 1990, 102, 1191; Angew. Chem. Int. Ed. Engl. 1990, 29, 1148-1150.
6. (b) Ebmeyer, F.; Rebek, J. Jr. Angew. Chem. 1990, 102, 1191; Angew. Chem. Int. Ed. Engl. 1990, 29, 1148-1150.
7. (c) Schneider, H.-J.; Ruf, D. Angew. Chem. 1990, 102, 1192; Angew. Chem. Int. Ed. Engl. 1990, 29, 1159-1160.
8. (c) Schneider, H.-J.; Ruf, D. Angew. Chem. 1990, 102, 1192; Angew. Chem. Int. Ed. Engl. 1990, 29, 1159-1160.
9. (d) Sijbesma, R. P.; Nolte, R. J. M. J. Am. Chem. Soc. 1991, 113, 6695-6696.
10. (e) Inouye, M.; Ueno, M.; Kitao, T. J. Org. Chem. 1992, 57, 1639-1641.
11. (f) Hayashi, T.; Asai, T.; Hokazono, H.; Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 12210-12211.
12. (g) Mizutani, T.; Yagi, S.; Honmaru, A.; Ogoshi, H. J. Am. Chem. Soc. 1996, 118, 5318-5319.
13. 4. (a) Bell, C. L.; Barrow, G. M. J. Chem. Phys. 1959, 5.
14. (b) Baba, H.; Matsuyama, A.; Kokubun, H. J. Chem. Phys. 1964, 41, 895-6.
15. (c) Gurka, D.; Taft, R. W.; Joris, L.; Schleyer, P. v. J. Am. Chem. Soc. 1967, 89, 5957-5958.
16. (d) Scott, R.; Palma, D. D.; Vinogradov, S. J. Phys. Chem. 1968, 72, 3192-3201.
17. (e) Scott, R.; Vinogradov, S. J. Phys. Chem. 1969, 73, 1890-1897.
18. (f) Hudson, R. A.; Scott, R. M.; Vinogradov, S. N. J. Phys. Chem. 1972, 76, 1989-1993.
19. (g) Crooks, J. E.; Robinson, B. H. Faraday Symp. Chem. Soc. 1975, 10, 29-40.
20. (h) Libus, W.; Mecik, M.; Sulek, W. J. Solution Chem. 1977, 6, 865-879.
21. (i) Koll, A.; Rospenk, M.; Sobczyk, L. J. Chem. Soc., Faraday Trans. 1 1981, 77, 2309-2314.
22. (j) Albrecht, G.; Zundel, G. J. Chem. Soc., Faraday Trans. 1 1984, 80, 553-561.
23. (k) Dwivedi, P. C.; Banga, A. K.; Sharma, N. Spectrochimica Acta 1986, 42A, 623-629.
24. (l) Kramer, R.; Zundel, G. J. Chem. Soc., Faraday Trans. 1990, 86, 301-305.
25. (m) Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630-7645.
26. 3 and toluene.
27. 6. Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754-5756.
28. -1 in cyclohexane at 25 °C. Induced CD was observed at 305 nm (Δε = -0.3) and at 273 nm (Δε = -0.4).
29. 8. We reported that, in a simplified system, the induced chirality varies as the bulkiness of substituents varied, see Mizutani, T.; Takagi, H.; Ogoshi, H. Tetrahedron Lett. 1996, 37, 2581-2584.