Enantioselective esterification of prochiral phosphonate pendants of a polyphenylacetylene assisted by macromolecular helicity: Storage of a dynamic macromolecular helicity memory

Journal of the American Chemical Society

Volumn 127, Issue 9, 2005, Pages 2960-2965

  Onouchi, Hisanari ^a   Miyagawa, Toyoharu ^b   Furuko, Akira ^a   Maeda, Katsuhiro ^a   Yashima, Eiji ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; OPTICAL PROPERTIES; ORGANIC ACIDS; ORGANIC POLYMERS; THERMOANALYSIS;

ACHIRAL DIAMINES; HELICAL STRUCTURE; MACROMOLECULAR HELICITY; PHOSPHONIC ACID;

ESTERIFICATION;

ACETYLENE DERIVATIVE; DIAZOMETHANE; ESTER DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; POLYMER; POLYPHENYLACETYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONFORMATION; ENANTIOSELECTIVITY; ESTERIFICATION; LOW TEMPERATURE; OPTICAL ROTATION;

EID: 14844320755     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042806v     Document Type: Article

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38. For chirality memory effect in supramolecular chemistry, see: (a) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119, 5267-5268. (b) Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Robertson, A.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1999, 3259-3264. (c) Prins, L. J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. (d) Kubo, Y.; Ohno, T.; Yamanaka, J.; Tokita, T.; Iida, T.; Ishimaru, Y. J. Am. Chem. Soc. 2001, 123, 12700-12701. (e) Lauceri, R.; Raudino, A.; Scolaro, L. M.; Micali, N.; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894-895. (f) Ishi-i, T.; Crego-Calama, M.; Timmerman, P.; Reinhoudt, D. N.; Shinkai, S. J. Am. Chem. Soc. 2002, 124, 14631-14641. For macromolecular helicity memory effect, see: (g) Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451. (h) Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342. (i) Onouchi, H.; Kashiwagi, D.; Hayashi, K.; Maeda, K.; Yashima, E. Macromolecules 2004, 37, 5495-5503. For reviews of chiral memory effects, see: (j) Purrello, R. Nat. Mater. 2003, 2, 216-217. (k) Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Soc. Rev. 2004, 33, 363-372.
39. For chirality memory effect in supramolecular chemistry, see: (a) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119, 5267-5268. (b) Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Robertson, A.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1999, 3259-3264. (c) Prins, L. J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. (d) Kubo, Y.; Ohno, T.; Yamanaka, J.; Tokita, T.; Iida, T.; Ishimaru, Y. J. Am. Chem. Soc. 2001, 123, 12700-12701. (e) Lauceri, R.; Raudino, A.; Scolaro, L. M.; Micali, N.; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894-895. (f) Ishi-i, T.; Crego-Calama, M.; Timmerman, P.; Reinhoudt, D. N.; Shinkai, S. J. Am. Chem. Soc. 2002, 124, 14631-14641. For macromolecular helicity memory effect, see: (g) Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451. (h) Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342. (i) Onouchi, H.; Kashiwagi, D.; Hayashi, K.; Maeda, K.; Yashima, E. Macromolecules 2004, 37, 5495-5503. For reviews of chiral memory effects, see: (j) Purrello, R. Nat. Mater. 2003, 2, 216-217. (k) Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Soc. Rev. 2004, 33, 363-372.
40. For chirality memory effect in supramolecular chemistry, see: (a) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119, 5267-5268. (b) Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Robertson, A.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1999, 3259-3264. (c) Prins, L. J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. (d) Kubo, Y.; Ohno, T.; Yamanaka, J.; Tokita, T.; Iida, T.; Ishimaru, Y. J. Am. Chem. Soc. 2001, 123, 12700-12701. (e) Lauceri, R.; Raudino, A.; Scolaro, L. M.; Micali, N.; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894-895. (f) Ishi-i, T.; Crego-Calama, M.; Timmerman, P.; Reinhoudt, D. N.; Shinkai, S. J. Am. Chem. Soc. 2002, 124, 14631-14641. For macromolecular helicity memory effect, see: (g) Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451. (h) Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342. (i) Onouchi, H.; Kashiwagi, D.; Hayashi, K.; Maeda, K.; Yashima, E. Macromolecules 2004, 37, 5495-5503. For reviews of chiral memory effects, see: (j) Purrello, R. Nat. Mater. 2003, 2, 216-217. (k) Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Soc. Rev. 2004, 33, 363-372.
41. For chirality memory effect in supramolecular chemistry, see: (a) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119, 5267-5268. (b) Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Robertson, A.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1999, 3259-3264. (c) Prins, L. J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. (d) Kubo, Y.; Ohno, T.; Yamanaka, J.; Tokita, T.; Iida, T.; Ishimaru, Y. J. Am. Chem. Soc. 2001, 123, 12700-12701. (e) Lauceri, R.; Raudino, A.; Scolaro, L. M.; Micali, N.; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894-895. (f) Ishi-i, T.; Crego-Calama, M.; Timmerman, P.; Reinhoudt, D. N.; Shinkai, S. J. Am. Chem. Soc. 2002, 124, 14631-14641. For macromolecular helicity memory effect, see: (g) Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451. (h) Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342. (i) Onouchi, H.; Kashiwagi, D.; Hayashi, K.; Maeda, K.; Yashima, E. Macromolecules 2004, 37, 5495-5503. For reviews of chiral memory effects, see: (j) Purrello, R. Nat. Mater. 2003, 2, 216-217. (k) Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Soc. Rev. 2004, 33, 363-372.
42. For chirality memory effect in supramolecular chemistry, see: (a) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119, 5267-5268. (b) Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Robertson, A.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1999, 3259-3264. (c) Prins, L. J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. (d) Kubo, Y.; Ohno, T.; Yamanaka, J.; Tokita, T.; Iida, T.; Ishimaru, Y. J. Am. Chem. Soc. 2001, 123, 12700-12701. (e) Lauceri, R.; Raudino, A.; Scolaro, L. M.; Micali, N.; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894-895. (f) Ishi-i, T.; Crego-Calama, M.; Timmerman, P.; Reinhoudt, D. N.; Shinkai, S. J. Am. Chem. Soc. 2002, 124, 14631-14641. For macromolecular helicity memory effect, see: (g) Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451. (h) Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342. (i) Onouchi, H.; Kashiwagi, D.; Hayashi, K.; Maeda, K.; Yashima, E. Macromolecules 2004, 37, 5495-5503. For reviews of chiral memory effects, see: (j) Purrello, R. Nat. Mater. 2003, 2, 216-217. (k) Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Soc. Rev. 2004, 33, 363-372.
43. For chirality memory effect in supramolecular chemistry, see: (a) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119, 5267-5268. (b) Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Robertson, A.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1999, 3259-3264. (c) Prins, L. J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. (d) Kubo, Y.; Ohno, T.; Yamanaka, J.; Tokita, T.; Iida, T.; Ishimaru, Y. J. Am. Chem. Soc. 2001, 123, 12700-12701. (e) Lauceri, R.; Raudino, A.; Scolaro, L. M.; Micali, N.; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894-895. (f) Ishi-i, T.; Crego-Calama, M.; Timmerman, P.; Reinhoudt, D. N.; Shinkai, S. J. Am. Chem. Soc. 2002, 124, 14631-14641. For macromolecular helicity memory effect, see: (g) Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451. (h) Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342. (i) Onouchi, H.; Kashiwagi, D.; Hayashi, K.; Maeda, K.; Yashima, E. Macromolecules 2004, 37, 5495-5503. For reviews of chiral memory effects, see: (j) Purrello, R. Nat. Mater. 2003, 2, 216-217. (k) Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Soc. Rev. 2004, 33, 363-372.
44. For chirality memory effect in supramolecular chemistry, see: (a) Furusho, Y.; Kimura, T.; Mizuno, Y.; Aida, T. J. Am. Chem. Soc. 1997, 119, 5267-5268. (b) Sugasaki, A.; Ikeda, M.; Takeuchi, M.; Robertson, A.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1 1999, 3259-3264. (c) Prins, L. J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. (d) Kubo, Y.; Ohno, T.; Yamanaka, J.; Tokita, T.; Iida, T.; Ishimaru, Y. J. Am. Chem. Soc. 2001, 123, 12700-12701. (e) Lauceri, R.; Raudino, A.; Scolaro, L. M.; Micali, N.; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894-895. (f) Ishi-i, T.; Crego-Calama, M.; Timmerman, P.; Reinhoudt, D. N.; Shinkai, S. J. Am. Chem. Soc. 2002, 124, 14631-14641. For macromolecular helicity memory effect, see: (g) Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451. (h) Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342. (i) Onouchi, H.; Kashiwagi, D.; Hayashi, K.; Maeda, K.; Yashima, E. Macromolecules 2004, 37, 5495-5503. For reviews of chiral memory effects, see: (j) Purrello, R. Nat. Mater. 2003, 2, 216-217. (k) Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. Chem. Soc. Rev. 2004, 33, 363-372.
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59. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
60. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
61. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
62. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
63. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
64. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
65. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
66. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
67. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
68. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
69. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
70. For other optically active polyacetylenes, see: (i) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179. (j) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390. (k) Moore, J. S.; Gorman, C. B.; Grubbs, R. H. J. Am. Chem. Soc. 1991, 113, 1704-1712. (l) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261-2262. (m) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009-2012. (n) Nomura, R.; Fukushima, Y.; Nakako, H.; Masuda, T. J. Am. Chem. Soc. 2000, 122, 8830-8836. (o) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160. (p) Schenning, A. P. H. J.; Fransen, M.; Meijer, E. W. Macromol. Rapid Commun. 2002, 23, 265-270. (q) Percec, V.; Obata, M.; Rudick, J. G.; De, B. B.; Glodde, M.; Bera, T. K.; Magonov, S. N.; Balagurusamy, V. S. K.; Heiney, P. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533. For reviews of dynamic helical polymers, see refs 1e, 5g, and 7 and: (r) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154. (s) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563. (t) Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
71. 4 and 3.5, respectively, as its methyl ester by size exclusion chromatography (SEC) with poly(ethylene oxide) and poly-(ethylene glycol) standards in DMF containing 10 mM lithium chloride.
72. (a) Manabe, K.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 6940-6941.
73. (b) Manabe, K.; Okamura, K.; Date, T.; Koga, K. J. Org. Chem. 1993, 58, 6692-6700.
74. (a) Hoffmann, M.; Wasielewski, C. Roczniki Chem. 1976, 50, 139-146.
75. (b) Macomber, R. S. Synth. Commun. 1977, 7, 405-407.
76. Jankowski, S.; Keglevich, G.; Nonas, T.; Forintos, H.; Glówka, M.; Rudzinski, J. Tetrahedron 2004, 60, 2789-2797.
77. Onouchi, H.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2001, 123, 7441-7442.
78. The methylation of L-menthyl phenylphosphonate with diazomethane was also reported to yield 50:50 mixtures of the diastereomers; see ref 12c.
79. Green, M. M.; Garetz, B. A.; Munoz, B.; Chang, H.; Hoke, S.; Cook, R. G. J. Am. Chem. Soc. 1995, 117, 4181-4182.
80. There is another possibility to explain the positive nonlinear effect: the helical poly-1 may act as a chiral filter to exclude one enantiomer for nonracemic amines; in other words, the helical poly-1 enantioselectively adsorbs one of the enantiomers 2. However, this possibility was excluded on the basis of the ee determination results of the bound 2 to poly-1 (see Supporting Information).
81. For chiral amplification in asymmetric synthesis with nonracemic polypeptides as catalysts, see: Kelly, D. R.; Meek, A.; Roberts, S. M. Chem. Commun. 2004, 2021-2022.
82. Morino, K.; Watase, N.; Maeda, K.; Yashima, E. Chem. - Eur. J. 2004, 10, 4703-4707.
83. 2nd value of poly-4a obtained from poly-1 with 0.3 equiv (R)-2 was 0.44 (see Figure 3b at [NMA]/[poly-1] = 0).
84. The recovery of (R)-2 (100%) was estimated based on the UV spectrum of the recovered (R)-2 in DMSO, which had been obtained by evaporating the solvents in the supernatant, followed by dilution with DMSO.
85. 6g-i,18 and the memorized poly-1 was treated with diazomethane. However, the reaction was not complete and yielded complex mixtures. Therefore, the isolated poly-1-3 complex was used for the esterification reaction with diazomethane.
86. 2nd value of 0.63 was quantitatively obtained.
87. For asymmetric synthesis with helical polymers as chiral ligands, see: Reggelin, M.; Doerr, S.; Klussmann, M.; Schultz, M.; Holbach, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5461-5466.
88. The optically pure (-)-4 (99.7% ee) was obtained by resolution of racemic 4 by HPLC on a preparative Chiralcel OD column. The absolute configuration of (-)-4 was tentatively assigned to be R based on the optical rotation sign of an analogous compound, (R)-(-)-ethyl methyl phenylphosphonate. See: DeBruin, K. D.; Tang, C. W.; Johnson, D. M.; Wilde, R. L. J. Am. Chem. Soc. 1989, 111, 5871-5879.
89. The concentrations of polymers at -95°C were corrected using the reported density value of methanol at -95°C. See: Brunel, R. F.; Bibber, K. V. In International Critical Tables of Numerical Data, Physics, Chemistry, and Technology; Washburn, E. W., Ed.; McGraw-Hill: New York, 1928; Vol. 3, p 27.
90. The absorption spectra of poly-4 and poly-1 complexed with (R)-2 are different from one another; the absorption spectrum of poly-4 exhibited a large red shift, the absorbance over 400 nm increased, and a peak at around 330 nm diminished (see Figure S-4 in the Supporting Information). These differences in their absorption spectra indicate that poly-1 complexed with (R)-2 may have a more tightly twisted helical conformation than that of poly-4, probably because of the bulkiness of (R)-2 complexed with the pendants of poly-1. Therefore, the maximum CD intensities of the poly-1-(R)-2 complex and poly-4 with a complete single-handed helix may be different from each other due to their different helical conformations.
91. 7,9i
92. (a) Nonokawa, R.; Yashima, E. J. Am. Chem. Soc. 2003, 125, 1278-1283.
93. (b) Nonokawa, R.; Oobo, M.; Yashima, E. Macromolecules 2003, 36, 6599-6606.