Reviews

Supramolecular Photochirogenesis with Cyclodextrins

  • Yao Jiabin ,
  • Xu Mengyu ,
  • Yan Zhiqiang ,
  • Wu Wanhua ,
  • Yang Cheng
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  • College of Chemistry, Sichuan University, Chengdu 610064

Received date: 2013-08-29

  Revised date: 2013-10-14

  Online published: 2013-10-31

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21372165, 23321061).

Abstract

In the present paper, supramolecular chiral photoreactions using cyclodextrins (CDs) as chiral inductors, including monomolecular photochirogenic reactions, bimolecular photochirogenic reactions, photochemical catalysis as well as the wavelength effects in photochirogenesis, have been summarized. This review focused on the binding behavior of CDs with different photosubstrates, the characteristics of chiral photoreactions mediated by CDs, the products distribution and stereoselectivity of chiral photoreactions with CDs and their working mechanisms. This paper concluded the advantages of CDs as host molecules used for chiral photoreactions, the problems existing in these supramolecular photochirogenesis systems and the perspective in this multidisciplinary research field.

Cite this article

Yao Jiabin , Xu Mengyu , Yan Zhiqiang , Wu Wanhua , Yang Cheng . Supramolecular Photochirogenesis with Cyclodextrins[J]. Chinese Journal of Organic Chemistry, 2014 , 34(1) : 26 -35 . DOI: 10.6023/cjoc201308038

References

[1] (a) Griesbeck, A.G.; Mattay, J. Synthetic Organic Photochemistry, Marcel Dekker, New York, 2005.
(b) Hu, R.; Zhang, C.; Pei, Z. Acta Chim. Sinica 2013, 71, 1064 (in Chinese).
(胡锐, 张承平, 裴志胜, 化学学报, 2013, 71, 1064.;
c) Tong, L., Lu, R., Inoue, Y. Prog. Chem. 2006, 18, 533 (in Chinese).
(童林荟, 鲁润华, 井上佳久, 化学进展, 2006, 18, 533.;
d) Lv, F.; Wu, L.; Zhang, L.; Tong, Z.; Zheng, L. Chin. J. Org. Chem. 2006, 26, 599 (in Chinese).
(吕峰峰, 吴骊珠, 张丽萍, 佟振合, 郑利强, 有机化学, 2006, 26, 599.;
e) Ma, L.; Chen, B.; Wu, L.; Peng, L.; Zhang, L.; Tong, Z. Prog. Chem. 2004, 16, 386 (in Chinese).
(马磊, 陈彬, 吴骊珠, 彭明丽, 张丽萍, 佟振合, 化学进展, 2004, 16, 386.;
f) Yang, C.; Inoue, Y. Chem. Soc. Rev. 2014, Advance Article, DOI: 10.1039/C3CS60339C.
[2] Inoue, Y.; Ramamurthy, V. Chiral Photochemistry, Marcel-Dekker, New York, 2004.
[3] Yang, C. Chin. Chem. Lett. 2013, 24, 437.
[4] Yang,C.; Inoue, Y. In Supramolecular Photochemistry: Controlling Photochemical Processes, Eds.: Ramamurthy, V.; Inoue, Y., John Wiley & Sons, Inc., Hoboken, 2011, p. 115.
[5] Yang, C.; Inoue, Y. In CRC Handbook of Organic Photochemistry and Photobiology, 3rd ed., Vol. 1, Eds.: Griesbeck, A. G.; Oelgemoller, M.; Ghetti, F.; Taylaor & Francis Group, Boca Raton, 2012, p. 125.
[6] Leibovitch, M.; Olovsson, G.; Sundarababu, G.; Ramamurthy, V.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1996, 118, 1219.
[7] Inoue, Y.; Dong, S. F.; Yamamoto, K.; Tong, L.-H.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1995, 113, 2793.
[8] Bach, T.; Bergmann, H.; Harms, K. Angew. Chem., Int. Ed. 2000, 39, 2302.
[9] Bach, T.; Bergmann, H.; Grosch, B.; Harms, K. J. Am. Chem. Soc. 2002, 124, 7982.
[10] shida, Y.; Kai, Y.; Kato, S.-Y.; Misawa, A.; Amano, S.; Matsuoka, Y.; Saigo, K. Angew. Chem., Int. Ed. 2008, 47, 8241.
[11] (a) Shirakawa, M.; Fujita, N.; Tani, T.; Kaneko, K.; Shinkai, S. Chem. Commun. 2005, 4149.
(b) Yin, Y.; Jie, J.; Diao, G. Chemistry 2009, 72, 320 (in Chinese).
(殷亚星, 解菊, 刁国旺, 化学通报, 2009, 72, 320.)
[12] Takahashi, K. Chem. Rev. 1998, 98, 2013.
[13] Vizvardi, K.; Desmet, K.; Luyten, I.; Sandra, P.; Hoornaert, G.; Van der Eycken, E. Org. Lett. 2001, 3, 1173.
[14] Koodanjeri, S.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9229.
[15] Koodanjeri, S.; Joy, A.; Ramamurthy, V. Tetrahedron 2000, 56, 7003.
[16] Shailaja, J.; Karthikeyan, S.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9335.
[17] Mori, T.; Wada, T.; Inoue, Y. Org. Lett. 2000, 2, 3401.
[18] Mori, T.; Inoue, Y.; Weiss, R. G. Org. Lett. 2003, 5, 4661.
[19] Mori, T.; Weiss, R. G.; Inoue, Y. J. Am. Chem. Soc. 2004, 126, 8961.
[20] Mori, T.; Saito, H.; Inoue, Y. Chem. Commun. 2003, 2302.
[21] Mori, T.; Takamoto, M.; Wada, T.; Inoue, Y. Photochem. Photobiol. Sci. 2003, 2, 1187.
[22] Rao, V. P.; Turro, N. J. Tetrahedron Lett. 1989, 30, 4641.
[23] Closs, G. L.; Paulson, D. R. J. Am. Chem. Soc. 1970, 92, 7229.
[24] Cocivera, M.; Trozzolo, A. M. J. Am. Chem. Soc. 1970, 92, 1772.
[25] Berger, M.; Goldblatt, I. L.; Steel, C. J. Am. Chem. Soc. 1973, 95, 1717.
[26] Tamaki, T.; Kokubu, T. J. Inclusion Phenom. Macrocyclic Chem. 1984, 2, 815.
[27] Tamaki, T.; Kokubu, T.; Ichimura, K. Tetrahedron Lett. 1987, 43, 1485.
[28] Wakai, A.; Fukasawa, H.; Yang, C.; Mori, T.; Inoue, Y. J. Am. Chem. Soc. 2012, 134, 4990.
[29] Ikeda, H.; Nihei, T.; Ueno, A. J. Org. Chem. 2005, 70, 1237.
[30] Yang, C.; Fukuhara, G.; Nakamura, A.; Origane, Y.; Fujita, K.; Yuan, D.-Q.; Mori, T.; Wada, T.; Inoue, Y. J. Photochem. Photobiol. A: Chem. 2005, 173, 375.
[31] Yang, C.; Nakamura, A.; Fukuhara, G.; Origane, Y.; Mori, T.; Wada, T.; Inoue, Y. J. Org. Chem. 2006, 71, 3126.
[32] (a) Yang, C.; Nakamura, A.; Wada, T.; Inoue, Y. Org. Lett. 2006, 8, 3005.
(b) Yang, C.; Mori, T.; Inoue, Y. J. Org. Chem. 2008, 73, 5786.
[33] Yang, C.; Ke, C.; Fujita, K.; Yuan, D.-Q.; Mori, T.; Inoue, Y. Aust. J. Chem. 2008, 1.
[34] Ke, C.; Yang, C.; Mori, T.; Wada, T.; Liu, Y.; Inoue, Y. Angew. Chem., Int. Ed. 2009, 48, 6675.
[35] Ke, C.; Yang, C.; Liang, W.; Mori, T.; Liu, Y.; Inoue, Y. New J. Chem. 2010, 34, 1323.
[36] Wang, Q.; Yang, C.; Fukuhara, G.; Mori, T.; Liu, Y.; Inoue, Y. Beilstein J. Org. Chem. 2011, 7, 290.
[37] Yang, C.; Nakamura, A.; Fukuhara, G.; Origane, Y.; Mori, T.; Wada, T.; Inoue, Y. J. Org. Chem. 2006, 71, 3126.
[38] Yang, C.; Ke, C.; Kahee, F.; Yuan, D.-Q.; Mori, T.; Inoue, Y. Aust. J. Chem. 2008, 61, 565.
[39] Ke, C.; Yang, C.; Mori, T.; Wada, T.; Liu, Y.; Inoue, Y. Angew. Chem., Int. Ed. Engl. 2009, 48, 6675.
[40] Fukuhara, G.; Umehara, H.; Higashino, S.; Nishijima, M.; Yang, C.; Mori, T.; Wada, T.; Inoue, Y. Photochem. Photobiol. Sci. 2013.
[41] Liao, G.-H.; Luo, L.; Xu, H.-X.; Wu, X.-L.; Lei, L.; Tung, C.-H.; Wu, L.-Z. J. Org. Chem. 2008, 73, 7345.
[42] Luo, L.; Cheng, S.-F.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Langmuir 2010, 26, 782.
[43] Liang, W.; Zhang, H.-H.; Wang, J.-J.; Peng, Y.; Chen, B.; Yang, C.; Tung, C.-H.; Wu, L.-Z.; Fukuhara, G.; Mori, T.; Inoue, Y. Pure Appl. Chem. 2011, 83, 769.
[44] Inoue, Y.; Kosaka, S.; Matsumoto, K.; Tsuneishi, H.; Hakushi, T.; Tai, A.; Nakagawa, K.; Tong, L. J. Photochem. Photobiol. A: Chem. 1993, 71, 61.
[45] Inoue, Y.; Wada, T.; Sugahara, N.; Yamamoto, K.; Kimura, K.; Tong, L.-H.; Gao, X.-M.; Hou, Z.-J.; Liu, Y. J. Org. Chem. 2000, 65, 8041.
[46] Fukuhara, G.; Mori, T.; Wada, T.; Inoue, Y. J. Org. Chem. 2006, 71, 8233.
[47] Lu, R.; Yang, C.; Cao, Y.; Wang, Z.; Wada, T.; Jiao, W.; Mori, T.; Inoue, Y. Chem. Commun. 2008, 2008, 374.
[48] Fukuhara, G.; Mori, T.; Wada, T.; Inoue, Y. Chem. Commun. 2005, 4199.
[49] Lu, R.; Yang, C.; Cao, Y.; Wang, Z.; Wada, T.; Jiao, W.; Mori, T.; Inoue, Y. J. Org. Chem. 2008, 7695.
[50] Gao, Y.; Wada, T.; Yang, K.; Kim, K.; Inoue, Y. Chirality 2005, 17, S19.
[51] Gao, Y.; Inoue, M.; Wada, T.; Inoue, Y. J. Inclusion Phenom. Macrocyclic Chem. 2004, 50, 111.
[52] ]Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1993, 58, 1011.
[53] Inoue, Y.; Ikeda, H.; Kaneda, M.; Sumimura, T.; Everitt, S. R. L.; Wada, T. J. Am. Chem. Soc. 2000, 122, 406.
[54] Inoue, Y. Sentan Kagaku Shirizu 2003, 1, 77.
[55] Kaneda, M.; Nishiyama, Y.; Asaoka, S.; Mori, T.; Wada, T.; Inoue, Y. Org. Biomol. Chem. 2004, 2, 1295.
[56] Inoue, Y. Kagaku Kogyo [Tokyo, Jap.] 2006, 59, 152.
[57] Inoue, Y.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1997, 119, 472.
[58] Yang, C.; Mori, T.; Wada, T.; Inoue, Y. New J. Chem. 2007, 31, 697.
[59] Wang, Q.; Yang, C.; Ke, C.; Fukuhara, G.; Mori, T.; Liu, Y.; Inoue, Y. Chem. Commun. 2011, 47, 6849.
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