Synthesis and chiroptical properties of axially chiral, binaphthol-based oligomers

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2979-2982

  Ng, Man Kit ^a   Chow, Hak Fun ^a   Chan, Tze Lock ^a   Mak, Thomas C W ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

binaphthol; optical active oligomers; optical activity

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0029971605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00478-9     Document Type: Article

References (22)

1. For reviews, see a) Ciardelli, F.; Chiellini, E.; Carlini, C.; Aglietto, M. Pure Appl. Chem. 1980, 52, 1857;
2. b) Wulff, G. Angew. Chem. Int. Ed. Engl. 1989, 28, 21;
3. c) Chapoy, L. L. Recent Advance in Liquid Crystalline Polymers, Elsevier, Amsterdam, 1985.
4. For examples, see a) Pino, P.; Lorenzi, G. P. J. Am. Chem. Soc. 1960, 82, 4745;
5. b) Abe, A.; Goodman, M. J. Polym. Sci. Part A: Polym. Chem. 1963, 1, 2193;
6. c) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174;
7. d) van Beijnen, A. J. M.; Nolte, R. J. M.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1980, 99, 121;
8. e) Green, M. M.; Andreola, C.; Muñoz, B.; Reidy, M. P.; Zero, K. J. Am. Chem. Soc. 1988, 110, 4063;
9. f) Ciardelli, F.; Aglietto, M.; Carlini, C.; Chiellini, E.; Solaro, R. Pure Appl. Chem. 1982, 54, 521.
10. Alzeer, J.; Vasella, A. Helv. Chim. Acta 1995, 78, 1219 and references cited therein.
11. In one of the cyclic binaphthol-containing oligomer series, the molar rotation is proportional to the number of chiral binaphthol groups inside the molecule. However, in another related series, no relationship could be established, see Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem. Int. Ed. Engl. 1995, 34, 1596.
12. Bedworth, P. V.; Tour, J. M. Macromolecules 1994, 27, 622.
13. Newman, M. S.; Sankaran, V.; Olson, D. R. J. Am. Chem. Soc. 1976, 98, 3237.
14. Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
15. 1H-NMR of the reaction product showed the presence of only 7a, the other diastereomer 7b could not be detected.
16. 0|).
17. Sheldrick, G. M. in Computational Crystallography (Ed: D. Sayre), Oxford University Press, New York, 1982, 506.
18. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
19. Hay, A. S. J. Org. Chem. 1960, 25, 1275.
20. +, 100%).
21. D of compounds 1 to 4 remain essential constant (± 2%) at different concentrations (c ranges from 0.03 to 1.18). Hence, the moderate optical activity enhancement observed here is not due to aggregation of different oligomers.
22. Monomer 1 can be considered as consisting of two 'independent' naphthol-monoacetylene chromophores due to the orthogonal disposition of the two naphthol rings. However, a new type of naphthol-diacetylene-naphthol chromophore is inserted between the two terminal naphthol-monoacetylene chromophores for oligomers 2-4.