Functionalized major-groove and minor-groove chiral polybinaphthyls: Application in the asymmetric reaction of aldehydes with diethylzinc

Journal of the American Chemical Society

Volumn 119, Issue 51, 1997, Pages 12454-12464

  Hu, Qiao Sheng ^a   Huang, Wei Sheng ^a   Vitharana, Dilrukshi ^a   Zheng, Xiao Fan ^a   Pu, Lin ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; NAPHTHYL GROUP; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; POLYMERIZATION; SYNTHESIS;

EID: 0031585735     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972623r     Document Type: Article

References (35)

1. Itsuno, S. In Polymeric Materials Encyclopedia; Synthesis, Properties and Applications; Salamone, J. C., Ed.; CRC Press: Boca Raton, FL, 1996; Vol. 10, p 8078.
2. Blossey, E. C.; Ford, W. T. In Comprehensive Polymer Science. The Synthesis, Characterization, Reactions and Applications of Polymers; Allen, G., Bevington, J. C., Eds.; Pergamon Press: New York, 1989; Vol. 6, pp 81.
3. Pittman, C. U. Jr. in Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1983; Vol. 8, pp 553.
4. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
5. Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
6. Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
7. (a) Hu, Q.-S.; Vitharana, D.; Liu, G.; Jain, V.; Wagaman, M. W.; Zhang, L.; Lee, T.; Pu, L. Macromolecules 1996, 29, 1082.
8. (b) Hu, Q.-S.; Vitharana, D.; Liu, G.; Jain, V.; Pu, L. Macromolecules 1996, 29, 5075.
9. Ma, L.; Hu, Q.-S.; Musick, K.; Vitharana, D.; Wu, C.; Kwan, C. M. S.; Pu, L. Macromolecules 1996, 29, 5083.
10. Ma, L.; Hu, Q.-S.; Vitharana, D.; Wu, C.; Kwan, C. M. S.; Pu, L. Macromolecules 1997, 30, 204.
11. For a review of chiral conjugated polymers, see: Pu, L. Acta Polymerica 1997, 48, 116.
12. (a) Hu, Q.-S.; Zheng, X.-F.; Pu, L. J. Org. Chem. 1996, 61, 5200.
13. (b) Hu, Q.-S.; Vitharana, D.; Zheng, X.-F.; Wu, C.; Kwan, C. M. S.; Pu, L. J. Org. Chem. 1996, 61, 8370.
14. A portion of this work has been communicated: Huang, W.-S.; Hu, Q.-S.; Zheng, X.-F.; Anderson, J.; Pu, L. J. Am. Chem. Soc. 1997, 119, 4313.
15. Huber, J.; Scherf, U. Macromol. Rapid Commun. 1994, 15, 897.
16. Selected references on the Suzuki coupling: (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
17. (b) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411.
18. (c) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
19. (a) Kyba, E. P.; Gokel, G. W.; Jong, F. de.; Koga, K.; Sousa, L. R.; Siegel M. G.; Kaplan, L.; Sogah, G. D. Y.; Cram, D. J. J. Org. Chem. 1977, 42, 4173.
20. (b) Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035.
21. Optically pure 1,1′-bi-2-naphthol can be conveniently obtained: Hu, Q-S.; Vitharana, D. R.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123.
22. (a) Kitajima, H.; Aoki, Y.; Ito, K.; Katsuki, T. Chem. Lett. 1995, 1113.
23. (b) Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 17, 2253.
24. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
25. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991; p 18.
26. Maruoka, K.; Murase, N.; Yamamoto, H. J. Org. Chem. 1993, 58, 2938
27. Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561.
28. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
29. Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
30. Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97.
31. Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710.
32. The reaction of diethylzinc with a binaphthol molecule containing 3,3′-bis(amide) groups has been studied. Formation of a trimeric binaphthylzinc complex is observed and its crystal structure is obtained: Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207.
33. Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
34. Sakane, S.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1985, 26, 5535.
35. Shoemaker, D. P.; Garland, C. W.; Nibler, J. W. Experiments in Physical Chemistry, 3rd ed.; McGraw-Hill: New York, 1996; p 179.