Poly(1,1′-bi-2-naphthol)s: Synthesis, characterization, and application in Lewis acid catalysis

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8370-8377

  Hu, Qiao Sheng ^a   Vitharana, Dilrukshi ^a   Zheng, Xiao Fan ^a   Wu, Chi ^b   Kwan, Chi Man Simon ^b   Pu, Lin ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000335614     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961407i     Document Type: Article

References (52)

1. (a) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
2. (b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
3. (c) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
4. (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 1.
5. (b) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
6. (c) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto. J. Am. Chem. Soc. 1988, 110, 310.
7. Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: New York, 1995.
8. Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3174.
9. Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
10. (a) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649.
11. (b) Carreira, E. M.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 12360.
12. Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571.
13. Hu, Q.-S.; Vitharana, D.; Liu, G.; Jain, V.; Wagaman, M. W.; Zhang, L.; Lee, T. ; Pu, L. Macromolecules 1996, 29, 1082.
14. Hu, Q.-S.; Vitharana, D.; Liu, G.; Jain, V.; Pu, L. Macromolecules 1996, 29, 5075.
15. Ma, L.; Hu, Q.-S.; Musick, K.; Vitharana, D.; Wu, C.; Kwan, C. M. S.; Pu, L. Macromolecules 1996, 29, 5083.
16. (a) Ma, L.; Hu, Q.-S.; Vitharana, D.; Pu, L. Polymer Prepr. 1996, 37(2), 462.
17. (b) Ma, L.; Hu, Q. -S.; Vitharana, D.; Wu, C.; Kwan, C. M. S.; Pu, L. Manuscript submitted.
18. (a) Blossey, E. C.; Ford, W. T. In Comprehensive Polymer Science. The Synthesis, Characterization, Reactions and Applications of Polymers; Allen, G., Bevington, J. C., Ed.; Pergamon Press: New York. 1989; Vol. 6, p 81.
19. (b) Pittman, C. U., Jr. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Ed.; Pergamon Press: Oxford, 1983; Vol. 8, p 553.
20. (a) Dumont, W.; Poulin, J. C.; Dang, T. P.; Kagan. H. B. J. Am. Chem. Soc. 1973, 95, 8295.
21. (b) Dang, T. P.; Kagan, H. B. Fr. Pat. 1 199 756.
22. Preliminary accounts of this work have been published: (a) Hu, Q.-S.; Zheng, X.-F.; Pu, L. J. Org. Chem. 1996, 61, 5200. (b) Vitharana, D.; Hu, Q.-S.; Pu, L. Polymer Prepr. 1996, 37(1), 855.
23. Preliminary accounts of this work have been published: (a) Hu, Q.-S.; Zheng, X.-F.; Pu, L. J. Org. Chem. 1996, 61, 5200. (b) Vitharana, D.; Hu, Q.-S.; Pu, L. Polymer Prepr. 1996, 37(1), 855.
24. (a) Pradellok, W.; Kotas, A.; Walczyk, W.; Jedlinski, Z. Chem. Abstr. 1979, 90, 121289t.
25. (b) Sogah, G. D. Y.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 3035.
26. An efficient resolution of 1,1′-bi-2-naphthol has been developed in this laboratory: Hu, Q.-S.; Vitharana, D. R.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123.
27. Maruyama, T.; Zhou, Z.; Kubota, K.; Yamamoto, T. Chem. Lett. 1992, 643.
28. Selected references on the Suzuki coupling reactions: (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513. (b) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411. (c) Huber, J.; Scherf, U. Macromol. Rapid Commun. 1994, 15, 897.
29. Selected references on the Suzuki coupling reactions: (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513. (b) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411. (c) Huber, J.; Scherf, U. Macromol. Rapid Commun. 1994, 15, 897.
30. Selected references on the Suzuki coupling reactions: (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513. (b) Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411. (c) Huber, J.; Scherf, U. Macromol. Rapid Commun. 1994, 15, 897.
31. Kitajima, H.; Aoki, Y.; Ito, K.; Katsuki, T. Chem. Lett. 1995, 1113.
32. (a) Wang, Y.; Quirk, R. P. Macromolecules 1995, 28, 3495.
33. (b) Phillips, R. W.; Sheares, V. V.; Samulski, E. T.; DeSimone, J. M. Macromolecules 1994, 27, 2354.
34. (a) Chu, B. Laser Light Scattering, 2nd ed.; Academic Press: New York, 1974.
35. (b) Pecora, R.; Berne, B. J. Dynamic Light Scattering. Plenum Press: New York, 1976.
36. (c) Wu, C.; Chan, K.; Xia, K. Q. Macromolecules 1995, 28, 1032.
37. Lingenfelter, D. S.; Helgeson, R. C.; Cram, D. J. J. Org. Chem. 1981, 46, 393.
38. Selected references on Lewis acid-catalyzed asymmetric Mukaiyama aldol condensations: (a) a review: Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Reetz, M. T.; Kyung, S.-H.; Bolm, C.; Zierke, T. Chem. Ind. 1986, 824. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (d) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. (e) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
39. Selected references on Lewis acid-catalyzed asymmetric Mukaiyama aldol condensations: (a) a review: Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Reetz, M. T.; Kyung, S.-H.; Bolm, C.; Zierke, T. Chem. Ind. 1986, 824. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (d) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. (e) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
40. Selected references on Lewis acid-catalyzed asymmetric Mukaiyama aldol condensations: (a) a review: Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Reetz, M. T.; Kyung, S.-H.; Bolm, C.; Zierke, T. Chem. Ind. 1986, 824. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (d) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. (e) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
41. Selected references on Lewis acid-catalyzed asymmetric Mukaiyama aldol condensations: (a) a review: Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Reetz, M. T.; Kyung, S.-H.; Bolm, C.; Zierke, T. Chem. Ind. 1986, 824. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (d) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. (e) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
42. Selected references on Lewis acid-catalyzed asymmetric Mukaiyama aldol condensations: (a) a review: Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Reetz, M. T.; Kyung, S.-H.; Bolm, C.; Zierke, T. Chem. Ind. 1986, 824. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (d) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. (e) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
43. Furuka, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041.
44. Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
45. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
46. (a) Terada, M.; Mikami, K.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1623.
47. (b) Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671.
48. (c) Kitamoto, D. H.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861.
49. References on Al-O-Al bridging bonds in aluminum alkoxide and aryloxide complexes: (a) Oliver, J. P.; Kumar, R.; Taghiof, M. In Coordination Chemistry of Aluminum; Robinson, G. H., Ed.; VCH Publishers: New York, 1993; p 167. (b) Jeffery, E. A.; Mole, T. Aust. J. Chem. 1968, 21, 2683. (c) Pasynkiewicz, S.; Starowieyski, K. B.; Skoweonska-Ptasinska, M. J. Organomet. Chem. 1973, 52, 269. (d) Pasynkiewicz, S.; Starowieyski, K. B.; Skoweonska-Ptasinska, M. J. Organomet. Chem. 1974, 65, 155.
50. References on Al-O-Al bridging bonds in aluminum alkoxide and aryloxide complexes: (a) Oliver, J. P.; Kumar, R.; Taghiof, M. In Coordination Chemistry of Aluminum; Robinson, G. H., Ed.; VCH Publishers: New York, 1993; p 167. (b) Jeffery, E. A.; Mole, T. Aust. J. Chem. 1968, 21, 2683. (c) Pasynkiewicz, S.; Starowieyski, K. B.; Skoweonska-Ptasinska, M. J. Organomet. Chem. 1973, 52, 269. (d) Pasynkiewicz, S.; Starowieyski, K. B.; Skoweonska-Ptasinska, M. J. Organomet. Chem. 1974, 65, 155.
51. References on Al-O-Al bridging bonds in aluminum alkoxide and aryloxide complexes: (a) Oliver, J. P.; Kumar, R.; Taghiof, M. In Coordination Chemistry of Aluminum; Robinson, G. H., Ed.; VCH Publishers: New York, 1993; p 167. (b) Jeffery, E. A.; Mole, T. Aust. J. Chem. 1968, 21, 2683. (c) Pasynkiewicz, S.; Starowieyski, K. B.; Skoweonska-Ptasinska, M. J. Organomet. Chem. 1973, 52, 269. (d) Pasynkiewicz, S.; Starowieyski, K. B.; Skoweonska-Ptasinska, M. J. Organomet. Chem. 1974, 65, 155.
52. References on Al-O-Al bridging bonds in aluminum alkoxide and aryloxide complexes: (a) Oliver, J. P.; Kumar, R.; Taghiof, M. In Coordination Chemistry of Aluminum; Robinson, G. H., Ed.; VCH Publishers: New York, 1993; p 167. (b) Jeffery, E. A.; Mole, T. Aust. J. Chem. 1968, 21, 2683. (c) Pasynkiewicz, S.; Starowieyski, K. B.; Skoweonska-Ptasinska, M. J. Organomet. Chem. 1973, 52, 269. (d) Pasynkiewicz, S.; Starowieyski, K. B.; Skoweonska-Ptasinska, M. J. Organomet. Chem. 1974, 65, 155.