Highly effective, easily accessible screw-sense-determining end group in the asymmetric polymerization of 1,2-diisocyanobenzenes

Organic Letters

Volumn 4, Issue 3, 2002, Pages 351-354

  Suginome, Michinori ^a   Collet, Sylvain ^a,b   Yoshihiko, Ito ^a,c  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITÉ DE NANTES   (France)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0042311020     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017113n     Document Type: Article

References (24)

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2. Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349. Noltle, R. J. M. Chem. Soc. Rev. 1994, 11. Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63.
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8. The screw-sense control by a sole chiral end group was demonstrated in nickel-catalyzed polymerization of monoisonitrile. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818.
9. Screw-sense control of conjugated polymers by other means have been reported. By chiral side chains, see: Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur. J. 2000, 6, 983. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895. By incorporation of configurationally stable axial chiralities in the main chains, see: Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore. J. S. J. Am. Chem. Soc. 1999, 121, 2643. By interaction of polymer side chains with optically active small molecules, see: Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. By chirality at the propagating living termini, see: Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926.
10. Screw-sense control of conjugated polymers by other means have been reported. By chiral side chains, see: Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur. J. 2000, 6, 983. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895. By incorporation of configurationally stable axial chiralities in the main chains, see: Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore. J. S. J. Am. Chem. Soc. 1999, 121, 2643. By interaction of polymer side chains with optically active small molecules, see: Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. By chirality at the propagating living termini, see: Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926.
11. Screw-sense control of conjugated polymers by other means have been reported. By chiral side chains, see: Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur. J. 2000, 6, 983. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895. By incorporation of configurationally stable axial chiralities in the main chains, see: Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore. J. S. J. Am. Chem. Soc. 1999, 121, 2643. By interaction of polymer side chains with optically active small molecules, see: Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. By chirality at the propagating living termini, see: Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926.
12. Screw-sense control of conjugated polymers by other means have been reported. By chiral side chains, see: Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur. J. 2000, 6, 983. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895. By incorporation of configurationally stable axial chiralities in the main chains, see: Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore. J. S. J. Am. Chem. Soc. 1999, 121, 2643. By interaction of polymer side chains with optically active small molecules, see: Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. By chirality at the propagating living termini, see: Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926.
13. Screw-sense control of conjugated polymers by other means have been reported. By chiral side chains, see: Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur. J. 2000, 6, 983. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895. By incorporation of configurationally stable axial chiralities in the main chains, see: Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore. J. S. J. Am. Chem. Soc. 1999, 121, 2643. By interaction of polymer side chains with optically active small molecules, see: Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. By chirality at the propagating living termini, see: Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926.
14. Screw-sense control of conjugated polymers by other means have been reported. By chiral side chains, see: Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur. J. 2000, 6, 983. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895. By incorporation of configurationally stable axial chiralities in the main chains, see: Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore. J. S. J. Am. Chem. Soc. 1999, 121, 2643. By interaction of polymer side chains with optically active small molecules, see: Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. By chirality at the propagating living termini, see: Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926.
15. Screw-sense control of conjugated polymers by other means have been reported. By chiral side chains, see: Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur. J. 2000, 6, 983. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895. By incorporation of configurationally stable axial chiralities in the main chains, see: Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore. J. S. J. Am. Chem. Soc. 1999, 121, 2643. By interaction of polymer side chains with optically active small molecules, see: Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. By chirality at the propagating living termini, see: Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926.
16. Screw-sense control of conjugated polymers by other means have been reported. By chiral side chains, see: Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur. J. 2000, 6, 983. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895. By incorporation of configurationally stable axial chiralities in the main chains, see: Dai, Y.; Katz, T. J. J. Org. Chem. 1997, 62, 1274. Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore. J. S. J. Am. Chem. Soc. 1999, 121, 2643. By interaction of polymer side chains with optically active small molecules, see: Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. By chirality at the propagating living termini, see: Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926.
17. (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
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19. (c) Shibasaki, M.; Sasai, H. Top. Stereochem. 1999, 22, 201.
20. (a) Kyba, E. B.; Koga, K.; Sousa, L. R.; Siegel, M. G.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 2692.
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22. 2P were used in the polymerization shown in Table 2.
23. For the ready preparation of o-(4,5-diphenylimidazolin-2-yl)iodobenzene from o-iodobenzoic acid with 1,2-diphenylethylenediamine, see Supporting Information.
24. 2PdI moieties at its termini, which was prepared from 6c with 2 equiv of 1a.