Recent progress in supramolecular chiral photochemistry

Chinese Chemical Letters

Volumn 24, Issue 6, 2013, Pages 437-441

  Yang, Cheng ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Photochemistry; Photochirogenesis; Stereochemistry; Supramolecular chemistry

Indexed keywords

EID: 84878498600     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.03.028     Document Type: Article

References (27)

1. E.L. Eliel, and S.H. Wilen Topics in Stereochemistry 2009 Wiley-Interscience
2. Y. Inoue, and V. Ramamurthy Chiral Photochemistry 2004 Marcel Dekker New York
3. Y. Inoue, T. Wada, and N. Sugahara Supramolecular photochirogenesis. 2. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-modified cyclodextrins J. Org. Chem. 65 2000 8041 8050
4. R. Lu, C. Yang, and Y. Cao Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by aroyl-β-cyclodextrins: a critical enantioselectivity control by substituents J. Org. Chem. 73 2008 7695 7701
5. C. Yang, T. Mori, T. Wada, and Y. Inoue Supramolecular enantiodifferentiating photoisomerization of (Z,Z)-1,3-cyclooctadiene included and sensitized by naphthalene-modified cyclodextrins New J. Chem. 31 2007 697 702
6. T. Tamaki, and T. Kokubu Acceleration of the photodimerization of water-soluble anthracenes included by b and g-cyclodextrins J. Incl. Phenom. Macro. 2 1984 815 821
7. A. Nakamura, and Y. Inoue Supramolecular catalysis of the enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate by g-cyclodextrin J. Am. Chem. Soc. 125 2003 966 974
8. C. Yang, G. Fukuhara, and A. Nakamura Enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate catalyzed by 6A,6X-diamino-6A,6X-dideoxy-g-cyclodextrins: manipulation of product chirality by electrostatic interaction, temperature and solvent in supramolecular photochirogenesis J. Photochem. Photobiol. A: Chem. 173 2005 375 384
9. H. Ikeda, T. Nihei, and A. Ueno Template-assisted stereoselective photocyclodimerization of 2-anthracenecarboxylic acid by bispyridinio-appended gamma-cyclodextrin J. Org. Chem. 70 2005 1237 1242
10. C. Yang, T. Mori, and Y. Inoue Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by capped γ-cyclodextrins: critical control of enantioselectivity by cap rigidity J. Org. Chem. 73 2008 5786 5794
11. C. Yang, T. Mori, and Y. Origane Highly stereoselective photocyclodimerization of a-cyclodextrin-appended anthracene mediated by g-cyclodextrin and cucurbit[8]uril: a dramatic steric effect operating outside the binding site J. Am. Chem. Soc. 130 2008 8574 8575
12. C. Yang, C. Ke, and W. Liang Dual supramolecular photochirogenesis: ultimate stereocontrol of photocyclodimerization by a chiral scaffold and confining host J. Am. Chem. Soc. 133 2011 13786 13789
13. L. Luo, G.H. Liao, X.L. Wu, L. Lei, C.H. Tung, and L.Z. Wu γ-Cyclodextrin-directed enantioselective photocyclodimerization of methyl 3-methoxyl-2-naphthoate J. Org. Chem. 74 2009 3506 3515
14. L. Luo, S.F. Cheng, B. Chen, C.H. Tung, and L.Z. Wu Stepwise photochemical-chiral delivery in γ-cyclodextrin-directed enantioselective photocyclodimerization of methyl 3-methoxyl-2-naphthoate in aqueous solution Langmuir 26 2010 197 249
15. W. Liang, H.H. Zhang, and J.J. Wang Supramolecular complexation and photocyclodimerization of methyl 3-methoxy-2-naphthoate with modified cyclodextrins Pure Appl. Chem. 83 2011 769-768
16. T. Bach, H. Bergmann, H. Brummerhop, W. Lewis, and K. Harms The [2+2]-photocycloaddition of aromatic aldehydes and ketones to 3,4-dihydro-2-pyridones: regioselectivity, diastereoselectivity, and reductive ring opening of the product oxetanes Chem. Eur. J. 7 2001 4512
17. T. Bach, H. Bergmann, B. Grosch, and K. Harms Highly enantioselective intra- and intermolecular [2+2] photocycloaddition reactions of 2-quinolones mediated by a chiral lactam host: host-guest interactions, product configuration, and the origin of the stereoselectivity in solution J. Am. Chem. Soc. 124 2002 7982 7983
18. A. Bauer, F. Westkämper, S. Grimme, and T. Bach Catalytic enantioselective reactions driven by photoinduced electron transfer Nature 436 2005 1139 1140
19. S. Breitenlechner, and T. Bach A polymer-bound chiral template for enantioselective photochemical reactions Angew. Chem. Inter. Ed. 47 2008 7957 7959
20. Y. Kawanami, T.C.S. Pace, and J.I. Mizoguchi Supramolecular complexation and enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid with 4-aminoprolinol derivatives as chiral hydrogen-bonding templates J. Org. Chem. 74 2009 7908 7921
21. T. Wada, N. Sugahara, M. Kawano, and Y. Inoue First asymmetric photochemistry with nucleosides and DNA: enantiodifferentiating Z-E photoisomerization of cyclooctene Chem. Lett. 2000 1174 1175
22. M. Nishijima, T.C.S. Pace, and A. Nakamura Supramolecular photochirogenesis with biomolecules. Mechanistic studies on the enantiodifferentiation for the photocyclodimerization of 2-anthracenecarboxylate mediated by bovine serum albumin J. Org. Chem. 72 2007 2707 2713
23. K. Bando, T. Zako, and M. Sakono Bio-supramolecular photochirogenesis with molecular chaperone: enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by prefoldin Photochem. Photobiol. Sci. 9 2010 655 660
24. Y. Ishida, Y. Kai, and S.Y. Kato Two-component liquid crystals as chiral reaction media: highly enantioselective photodimerization of an anthracene derivative driven by the ordered microenvironment Angew. Chem. Inter. Ed. 47 2008 8241 8245
25. F.F. Lv, B. Chen, L.Z. Wu, L.P. Zhang, and C.H. Tung Enhanced stereoselectivity in photoelectrocyclization of tropolone ethers via confinement in chiral inductor-modified lyotropic liquid crystals Org. Lett. 10 2008 3473 3476
26. A. Dawn, T. Shiraki, and S. Haraguchi Transcription of chirality in the organogel systems dictates the enantiodifferentiating photodimerization of substituted anthracene Chem. A Eur. J. 16 2010 3676 3689
27. Y. Nishioka, T. Yamaguchi, M. Kawano, and M. Fujita Asymmetric [2+2] olefin cross photoaddition in a self-assembled host with remote chiral auxiliaries J. Am. Chem. Soc. 130 2008 8160 8161