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Volumn , Issue 23, 2007, Pages 2351-2353

Macromolecular helicity inversion of an optically active helical poly(phenylacetylene) by chemical modification of the side groups

(3) Kobayashi, Shinzo a Morino, Kazuhide a Yashima, Eiji a

a NAGOYA UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; ESTER DERIVATIVE; HYDROXYL GROUP; ISOCYANATE; PHENYLACETYLENE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; POLYMERIZATION; SYNTHESIS;

EID: 34249989774 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b701281k Document Type: Article

Times cited : (14)

References (43)

1
- 0003610122
- Wiley VCH, Weinheim
- U. T. Bornscheuer and R. J. Kazulauskas, Hydrolases in Organic Synthesis, Wiley VCH, Weinheim, 1999
- (1999) Hydrolases in Organic Synthesis
- Bornscheuer, U.T.¹ Kazulauskas, R.J.²

2
- 0003479152
- Springer, New York, 5th edn, For recent reviews, see:
- K. Faber, Biotransformations in Organic Chemistry, Springer, New York, 5th edn, 2004
- (2004) Biotransformations in Organic Chemistry
- Faber, K.¹

3
- 0036525716
- M. T. Reetz Curr. Opin. Chem. Biol. 2002 6 145
- (2002) Curr. Opin. Chem. Biol. , vol.6 , pp. 145
- Reetz, M.T.¹

4
- 3042636458
- T. Ema Curr. Org. Chem. 2004 8 1009
- (2004) Curr. Org. Chem. , vol.8 , pp. 1009
- Ema, T.¹

5
- 10844227997
- For recent examples, see:
- A. Ghanem H. Y. Aboul-enein Chirality 2005 17 1
- (2005) Chirality , vol.17 , pp. 1
- Ghanem, A.¹ Aboul-Enein, H.Y.²

6
- 0042888728
- A. Ghanem V. Schurig Tetrahedron: Asymmetry 2003 14 2547
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2547
- Ghanem, A.¹ Schurig, V.²

7
- 9144261841
- T. Matsuda K. Watanabe T. Harada K. Nakamura Y. Arita Y. Misumi S. Ichikawa T. Ikariya Chem. Commun. 2004 2286
- (2004) Chem. Commun. , pp. 2286
- Matsuda, T.¹ Watanabe, K.² Harada, T.³ Nakamura, K.⁴ Arita, Y.⁵ Misumi, Y.⁶ Ichikawa, S.⁷ Ikariya, T.⁸

8
- 26944481501
- T. Ema T. Fujii M. Ozaki T. Korenaga T. Sakai Chem. Commun. 2005 4650
- (2005) Chem. Commun. , pp. 4650
- Ema, T.¹ Fujii, T.² Ozaki, M.³ Korenaga, T.⁴ Sakai, T.⁵

9
- 0034316816
- H. Kikuchi H. Uyama S. Kobayashi Macromolecules 2000 33 8971
- (2000) Macromolecules , vol.33 , pp. 8971
- Kikuchi, H.¹ Uyama, H.² Kobayashi, S.³

10
- 22744452041
- J. W. Peeters O. van Leeuwen A. R. A. Palmans E. W. Meijer Macromolecules 2005 38 5587
- (2005) Macromolecules , vol.38 , pp. 5587
- Peeters, J.W.¹ Van Leeuwen, O.² Palmans, A.R.A.³ Meijer, E.W.⁴

11
- 0033517692
- M. M. Green J.-W. Park T. Sato A. Teramoto S. Lifson R. L. B. Selinger J. V. Selinger Angew. Chem., Int. Ed. 1999 38 3138
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 3138
- Green, M.M.¹ Park, J.-W.² Sato, T.³ Teramoto, A.⁴ Lifson, S.⁵ Selinger, R.L.B.⁶ Selinger, J.V.⁷

12
- 0035781183
- T. Nakano Y. Okamoto Chem. Rev. 2001 101 4013
- (2001) Chem. Rev. , vol.101 , pp. 4013
- Nakano, T.¹ Okamoto, Y.²

13
- 0035542911
- J. J. L. M. Cornelissen A. E. Rowan R. J. M. Nolte N. A. J. M. Sommerdijk Chem. Rev. 2001 101 4039
- (2001) Chem. Rev. , vol.101 , pp. 4039
- Cornelissen, J.J.L.M.¹ Rowan, A.E.² Nolte, R.J.M.³ Sommerdijk, N.A.J.M.⁴

14
- 0038513716
- M. Fujiki J. R. Koe K. Terao T. Sato A. Teramoto J. Watanabe Polym. J. 2003 35 297
- (2003) Polym. J. , vol.35 , pp. 297
- Fujiki, M.¹ Koe, J.R.² Terao, K.³ Sato, T.⁴ Teramoto, A.⁵ Watanabe, J.⁶

15
- 33748854652
- K. Maeda E. Yashima Top. Curr. Chem. 2006 265 47
- (2006) Top. Curr. Chem. , vol.265 , pp. 47
- Maeda, K.¹ Yashima, E.²

16
- 0029636622
- E. Yashima S. Huang T. Matsushima Y. Okamoto Macromolecules 1995 28 4184
- (1995) Macromolecules , vol.28 , pp. 4184
- Yashima, E.¹ Huang, S.² Matsushima, T.³ Okamoto, Y.⁴

17
- 0037112686
- K. Morino K. Maeda Y. Okamoto E. Yashima T. Sato Chem.-Eur. J. 2002 8 5112
- (2002) Chem.-Eur. J. , vol.8 , pp. 5112
- Morino, K.¹ Maeda, K.² Okamoto, Y.³ Yashima, E.⁴ Sato, T.⁵

18
- 0037010851
- R. Nomura H. Nakako T. Masuda J. Mol. Catal. A: Chem. 2002 190 197
- (2002) J. Mol. Catal. A: Chem. , vol.190 , pp. 197
- Nomura, R.¹ Nakako, H.² Masuda, T.³

19
- 0037435643
- B. S. Li K. K. L. Cheuk L. Ling X. Xiao C. Bai B. Z. Tang Macromolecules 2003 36 77
- (2003) Macromolecules , vol.36 , pp. 77
- Li, B.S.¹ Cheuk, K.K.L.² Ling, L.³ Xiao, X.⁴ Bai, C.⁵ Tang, B.Z.⁶

20
- 23744460719
- M. Teraguchi K. Mottate S. Kim T. Aoki T. Kaneko S. Hadano T. Masuda Macromolecules 2005 38 6367
- (2005) Macromolecules , vol.38 , pp. 6367
- Teraguchi, M.¹ Mottate, K.² Kim, S.³ Aoki, T.⁴ Kaneko, T.⁵ Hadano, S.⁶ Masuda, T.⁷

21
- 20444438844
- J. Tabei M. Shiotsuki T. Sato F. Sanda T. Masuda Chem.-Eur. J. 2005 11 3591
- (2005) Chem.-Eur. J. , vol.11 , pp. 3591
- Tabei, J.¹ Shiotsuki, M.² Sato, T.³ Sanda, F.⁴ Masuda, T.⁵

22
- 27544455742
- Helical poly(phenylacetylene)s with a controlled helicity can also be prepared by the helix-sense-selective polymerization of an achiral phenylacetylene or based on the noncovalent helicity induction and chiral memory concept.
- V. Percec J. G. Rudick M. Peterca M. Wagner M. Obata C. M. Mitchell W.-D. Cho V. S. K. Balagurusamy P. A. Heiney J. Am. Chem. Soc. 2005 127 15257
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 15257
- Percec, V.¹ Rudick, J.G.² Peterca, M.³ Wagner, M.⁴ Obata, M.⁵ Mitchell, C.M.⁶ Cho, W.-D.⁷ Balagurusamy, V.S.K.⁸ Heiney, P.A.⁹

23
- 0038175503
- T. Aoki T. Kaneko N. Maruyama A. Sumi M. Takahashi T. Sato M. Teraguchi J. Am. Chem. Soc. 2003 125 6346
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 6346
- Aoki, T.¹ Kaneko, T.² Maruyama, N.³ Sumi, A.⁴ Takahashi, M.⁵ Sato, T.⁶ Teraguchi, M.⁷

24
- 0033519678
- E. Yashima K. Maeda Y. Okamoto Nature 1999 399 449
- (1999) Nature , vol.399 , pp. 449
- Yashima, E.¹ Maeda, K.² Okamoto, Y.³

25
- 1842607368
- K. Maeda K. Morino Y. Okamoto T. Sato E. Yashima J. Am. Chem. Soc. 2004 126 4329
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 4329
- Maeda, K.¹ Morino, K.² Okamoto, Y.³ Sato, T.⁴ Yashima, E.⁵

26
- 14844320755
- H. Onouchi T. Miyagawa A. Furuko K. Maeda E. Yashima J. Am. Chem. Soc. 2005 127 2960
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 2960
- Onouchi, H.¹ Miyagawa, T.² Furuko, A.³ Maeda, K.⁴ Yashima, E.⁵

27
- 17144364271
- T. Miyagawa A. Furuko K. Maeda H. Katagiri Y. Furusho E. Yashima J. Am. Chem. Soc. 2005 127 5018
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 5018
- Miyagawa, T.¹ Furuko, A.² Maeda, K.³ Katagiri, H.⁴ Furusho, Y.⁵ Yashima, E.⁶

28
- 33750884601
- For more details, see electronic supplementary information (ESI) According to Kazlauskas' rule, the R-secondary alcohols are preferentially esterified during the lipase-catalyzed kinetic resolution of racemic secondary alcohols. Therefore, the absolute configurations of the optically active 1 and 2 obtained by the kinetic resolution of rac- 1 with lipase were tentatively assigned as S and R, respectively. For Kazlauskas' rule, see:
- T. Hasegawa K. Maeda H. Ishiguro E. Yashima Polym. J. 2006 38 912
- (2006) Polym. J. , vol.38 , pp. 912
- Hasegawa, T.¹ Maeda, K.² Ishiguro, H.³ Yashima, E.⁴

29
- 0028134021
- Copolymerization results of (S)- 1 and (R)- 2 at varying monomer feed ratios ([(S)- 1]: [(R)- 2] = 1: 9, 3: 7, 5: 5, 7: 3, and 9: 1) showed that the polymerizability of (S)- 1 is almost identical to that of (R)- 2 and that the monomer distributions in the copolymer, poly((S)- 1-co-(R)- 2), are mostly random, independent of the level of monomer conversions
- M. Cygler P. Grochulski R. J. Kazlauskas J. D. Schrag F. Bouthillier B. Rubin A. N. Serreqi A. K. Gupta J. Am. Chem. Soc. 1994 116 3180
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 3180
- Cygler, M.¹ Grochulski, P.² Kazlauskas, R.J.³ Schrag, J.D.⁴ Bouthillier, F.⁵ Rubin, B.⁶ Serreqi, A.N.⁷ Gupta, A.K.⁸

30
- 34249990348
- The CD and absorption spectra of all the copolymers in THF did not change after the samples had been allowed to stand at room temperature for 1 day For recent reviews, see ref 4 and
- The CD and absorption spectra of all the copolymers in THF did not change after the samples had been allowed to stand at room temperature for 1 day

31
- 0034873438
- M. M. Green K.-S. Cheon S.-Y. Yang J.-W. Park S. Swansburg W. Liu Acc. Chem. Res. 2001 34 672
- (2001) Acc. Chem. Res. , vol.34 , pp. 672
- Green, M.M.¹ Cheon, K.-S.² Yang, S.-Y.³ Park, J.-W.⁴ Swansburg, S.⁵ Liu, W.⁶

32
- 26644441873
- For recent examples, see:
- J. W. Y. Lam B. Z. Tang Acc. Chem. Res. 2005 38 745
- (2005) Acc. Chem. Res. , vol.38 , pp. 745
- Lam, J.W.Y.¹ Tang, B.Z.²

33
- 0038450358
- K. Tang M. M. Green K. S. Cheon J. V. Selinger B. A. Garetz J. Am. Chem. Soc. 2003 125 7313
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 7313
- Tang, K.¹ Green, M.M.² Cheon, K.S.³ Selinger, J.V.⁴ Garetz, B.A.⁵

34
- 0037432369
- K. Morino K. Maeda E. Yashima Macromolecules 2003 36 1480
- (2003) Macromolecules , vol.36 , pp. 1480
- Morino, K.¹ Maeda, K.² Yashima, E.³

35
- 0346058163
- K. K. L. Cheuk J. W. Y. Lam L. M. Lai Y. Dong B. Z. Tang Macromolecules 2003 36 9752
- (2003) Macromolecules , vol.36 , pp. 9752
- Cheuk, K.K.L.¹ Lam, J.W.Y.² Lai, L.M.³ Dong, Y.⁴ Tang, B.Z.⁵

36
- 4644223898
- H. Ohira M. Kunitake M. Fujiki M. Naito A. Saxena Chem. Mater. 2004 16 3919
- (2004) Chem. Mater. , vol.16 , pp. 3919
- Ohira, H.¹ Kunitake, M.² Fujiki, M.³ Naito, M.⁴ Saxena, A.⁵

37
- 24344433235
- H. Zhao F. Sanda T. Masuda Macromol. Chem. Phys. 2005 206 1653
- (2005) Macromol. Chem. Phys. , vol.206 , pp. 1653
- Zhao, H.¹ Sanda, F.² Masuda, T.³

38
- 33646544017
- S. Sakurai K. Okoshi J. Kumaki E. Yashima J. Am. Chem. Soc. 2006 128 5650
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 5650
- Sakurai, S.¹ Okoshi, K.² Kumaki, J.³ Yashima, E.⁴

39
- 33745037692
- The significant difference between the CD spectrum of the sum of the homopolymers of poly((S)- 1) and poly((R)- 2) (1: 2 = 53: 47, mol/mol) and the CD spectrum of the copolymer (poly((S)- 1-co-(R)- 2)) (1: 2 = 53: 47, mol/mol) (Fig. S4A) indicates that the poly((S)- 1-co-(R)- 2)) is not composed of the blocks of poly((S)- 1) and poly((R)- 2). A similar great difference between the CD spectrum of poly((S)- 3-co-(R)- 2) and the sum of the CD spectra of the corresponding homopolymers, poly((S)- 3) and poly((R)- 2) (Fig. S4B), also supports the random monomer distributions in the poly((S)- 3-co-(R)- 2). These results clearly revealed the inversion of the helix-sense of the poly((S)- 1-co-(R)- 2) main-chain that takes place after the chemical modification of the hydroxy groups with bulky substituents The different temperature-dependent ICD intensity changes observed for the copolymers (Fig. 2B) may be determined by cooperative interactions with neighboring monomer units;
- K. Maeda H. Mochizuki M. Watanabe E. Yashima J. Am. Chem. Soc. 2006 128 7639
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 7639
- Maeda, K.¹ Mochizuki, H.² Watanabe, M.³ Yashima, E.⁴

40
- 26644464591
- N. Kim S.-B. Ko M. S. Kwon M.-J. Kim J. Park Org. Lett. 2005 7 4523
- (2005) Org. Lett. , vol.7 , pp. 4523
- Kim, N.¹ Ko, S.-B.² Kwon, M.S.³ Kim, M.-J.⁴ Park, J.⁵

41
- 21044443212
- For optically pure oligo- and polyester synthesis using DKR, see:
- B. Martin-Matute M. Edin K. Bogár F. B. Kaynak J.-E. Bäckvall J. Am. Chem. Soc. 2005 127 8817
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 8817
- Martin-Matute, B.¹ Edin, M.² Bogár, K.³ Kaynak, F.B.⁴ Bäckvall, J.-E.⁵

42
- 22244444234
- B. A. C. van As J. van Buijtenen A. Heise Q. B. Broxterman G. K. M. Verzijl A. R. A. Palmans E. W. Meijer J. Am. Chem. Soc. 2005 127 9964
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 9964
- Van As, B.A.C.¹ Van Buijtenen, J.² Heise, A.³ Broxterman, Q.B.⁴ Verzijl, G.K.M.⁵ Palmans, A.R.A.⁶ Meijer, E.W.⁷

43
- 33746458896
- J. van Buijtenen B. A. C. van As J. Meuldijk A. R. A. Palmans J. A. J. M. Vekemans L. A. Hulshof E. W. Meijer Chem. Commun. 2006 3169
- (2006) Chem. Commun. , pp. 3169
- Van Buijtenen, J.¹ Van As, B.A.C.² Meuldijk, J.³ Palmans, A.R.A.⁴ Vekemans, J.A.J.M.⁵ Hulshof, L.A.⁶ Meijer, E.W.⁷

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.