Abstract
A novel, optically active, cis-transoidal polyacetylene, poly[N-(4-ethynylbenzyl)ephedrine] (poly-4b) was prepared and interactions with chiral acids were examined by means of circular dichroism (CD) spectroscopy. The Intensity of induced CD of the polymer decreased with an increase in the concentration of (R)- or (S)-mandelic acid. However, significant differences between the induced CD changes in the presence of (R)- or (S)-mandelic acid were not found in the complexation. Poly-4b was used as an optically active catalyst for enantioselective addition of benzaldehyde with dialkylzincs. Enantiomeric excess of 1-phenylethanol obtained was 30–49%.
Similar content being viewed by others
Article PDF
References
Y. Okamoto and T. Nakano, Chem. Rev., 94, 349 (1994).
R. J. M. Nolte, Chem. Soc. Rev., 11 (1994).
M. M. Green, N. C. Peterson, T. Sato, A. Teramoto, R. Cook, and S. Lifson, Science, 268, 1860 (1995).
M. Qin, J. Bartus, and O. Vogl, Macromol. Symp., 98, 387 (1995).
L. Pu, Acta Polym., 48, 116 (1997).
S. Takahashi, K. Onitsuka, and F. Takei, Proc. Japan Acad., Ser. B, 74, 25 (1998).
K. Ute, K. Hirose, H. Kashimato, K. Hatada, and O. Vogl, J. Am. Chem. Soc., 113, 6305 (1991).
Y. Okamoto, M. Matsuda, T. Nakano, and E. Yashima, J. Polym. Sci., Part A, Polym. Chem., 32, 309 (1994).
Y. Ito, T. Miyake, S. Hatano, R. Shima, T. Ohara, and M. Suginome, J. Am. Chem. Soc., 120, 11880 (1998).
T. Nakano, Y. Okamoto, and K. Hatada, J. Am. Chem. Soc., 114, 1318 (1992).
E. Yashima, T. Matsushima, and Y. Okamoto, J. Am. Chem. Soc., 119, 6345 (1997).
E. Yashima, T. Nimura, T. Matsushima, and Y. Okamoto, J. Am. Chem. Soc., 118, 9800 (1996).
E. Yashima, Y. Maeda, T. Matsushima, and Y. Okamoto, Chirality, 9, 593 (1997).
E. Yashima, Y. Maeda, and Y. Okamoto, J. Am. Chem. Soc., 120, 8895 (1998).
K. Soai, S. Yokoyama, K. Ebihara, and T. Hayasaka, J. Chem. Soc., Chem. Commun., 1690 (1987).
K. Soai, S. Niwa, and M. Watanabe, J. Chem. Soc. Perkin Trans. 1, 109 (1989).
A. K. Ghosh, P. Mathivanan, and J. Cappiello, Tetrahedron Asym., 9, 1 (1998).
A. Furlani, C. Napoletano, M. Russo, A. Camus, and N. Marsich, J. Polym. Sci., Polym. Chem. Ed., 27, 75 (1989).
M. Tabata, W. Yang, and K. Yokota, Polym. J., 12, 1105 (1990).
C. Simionescu, S. Dumitrescu, and V. Percec, J. Polym. Sci., Polym. Symp., 64, 209 (1978).
A. Furlani, C. Napoletano, M. V. Russo, and W. J. Feast, Polym. Bull., 16, 311 (1986).
S. Matsunami, T. Kakuchi, and F. Ishii, Macromolecules, 30, 1074 (1997).
W.-S. Huang, Q.-S. Hu, X.-F. Zhang, J. Anderson, and L. Pu, J. Am. Chem. Soc., 119, 4313 (1997).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Yashima, E., Maeda, Y. & Okamoto, Y. Synthesis of Poly[N-(4-ethynylbenzyl)ephedrine] and Its Use as a Polymeric Catalyst for Enantioselective Addition of Dialkylzincs to Benzaldehyde. Polym J 31, 1033–1036 (1999). https://doi.org/10.1295/polymj.31.1033
Issue Date:
DOI: https://doi.org/10.1295/polymj.31.1033
Keywords
This article is cited by
-
Helical Polyacetylenes Induced via Noncovalent Chiral Interactions and Their Applications as Chiral Materials
Topics in Current Chemistry (2017)
-
Graft of chiral amino alcohol onto poly(menthyl vinyl ketone) and the grafted polymer’s inducement to the asymmetric addition of phenylacetylene to aromatic ketone
Chemical Research in Chinese Universities (2015)
-
Redox-responsive molecular helices with highly condensed π-clouds
Nature Chemistry (2011)
-
Asymmetric anionic polymerization of N-substituted maleimides bearing an azo group with chiral anionic initiators
Polymer Journal (2011)