Sunday, October 2, 2022
HomeChemistrySynthesis of cyclodextrin derivatives for enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate

Synthesis of cyclodextrin derivatives for enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate


  • Rau, H. Uneven photochemistry in answer. Chem. Rev. 83, 535–547 (1983).

    CAS 
    Article 

    Google Scholar
     

  • Inoue, Y. Uneven photochemical reactions in answer. Chem. Rev. 92, 741–770 (1992).

    CAS 
    Article 

    Google Scholar
     

  • Griesbeck, A. G. & Meierhenrich, U. J. Uneven photochemistry and photochirogenesis. Angew. Chem. Int. Ed. 41, 3147–3154 (2002).

    Article 

    Google Scholar
     

  • Inoue, Y. & Ramamurthy, V. (eds.) Chiral Photochemistry (CRC Press, 2004).

  • Yang, C. & Inoue, Y. Supramolecular photochirogenesis. in Supramolecular Photochemistry (eds Ramamurthy, V. & Inoue, Y.) 4.115–4.153 (Wiley, 2011).

  • Yang, C. Latest progress in supramolecular chiral photochemistry. Chin. Chem. Lett. 24, 437–441 (2013).

    Article 
    CAS 

    Google Scholar
     

  • Yang, C. & Inoue, Y. Supramolecular photochirogenesis. Chem. Soc. Rev. 43, 4123–4143 (2014).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Ramamurthy, V. & Gupta, S. Supramolecular photochemistry: from molecular crystals to water-soluble capsules. Chem. Soc. Rev. 44, 119–135 (2015).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Morimoto, M. et al. Advances in supramolecular host-mediated reactivity. Nat. Catal. 3, 969–984 (2020).

    CAS 
    Article 

    Google Scholar
     

  • Yao, J. et al. Ammonia-driven chirality inversion and enhancement in enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by diguanidino-γ-cyclodextrin. J. Am. Chem. Soc. 136, 6916–6919 (2014).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Rao, M. et al. Photocatalytic supramolecular enantiodifferentiating dimerization of 2-anthracenecarboxylic acid via triplet–triplet annihilation. Org. Lett. 20, 1680–1683 (2018).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Wei, X. et al. Supramolecular photochirogenesis pushed by higher-order complexation: enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate to slipped cyclodimers through a 2:2 advanced with β-cyclodextrin. J. Am. Chem. Soc. 140, 3959–3974 (2018).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Ji, J. et al. An final stereocontrol in supramolecular photochirogenesis: Photocyclodimerization of 2-anthracenecarboxylate mediated by sulfur-linked β-cyclodextrin dimers. J. Am. Chem. Soc. 141, 9225–9238 (2019).

    PubMed 
    Article 
    CAS 

    Google Scholar
     

  • Wang, Q. et al. A supramolecular technique for enhancing photochirogenic efficiency via host/visitor modification: dicationic γ-cyclodextrin-mediated photocyclodimerization of two,6-anthracenedicarboxylate. Org. Lett. 14, 9757–9761 (2020).

    Article 
    CAS 

    Google Scholar
     

  • Kanagaraj, Ok. et al. pH-controlled chirality inversion in enantiodifferentiating photocyclodimerization of 2-antharacenecarboxylic acid mediated by γ-cyclodextrin derivatives. Org. Lett. 22, 5273–5278 (2020).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Luo, L. et al. Cyclodextrin-directed enantioselective photocyclodimerization of methyl 3-methoxyl-2-naphthoate. J. Org. Chem. 74, 3506–3515 (2009).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Brimioulle, R. & Bach, T. Enantioselective lewis acid catalysis of intramolecular enone [2 + 2] photocycloaddition reactions. Science 342, 840–843 (2013).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Coote, S. C. & Bach, T. Enantioselective intermolecular [2 + 2] photocycloadditions of isoquinolone mediated by a chiral hydrogen-bonding template. J. Am. Chem. Soc. 135, 14948–14951 (2013).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Kawanami, Y. et al. Supramolecular photochirogenesis with a higher-order advanced: Extremely accelerated solely head-to-head photocyclodimerization of 2-anthracenecarboxylic acid through 2:2 complexation with prolinol. J. Am. Chem. Soc. 138, 12187–12201 (2016).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Skubi, Ok. L. et al. Enantioselective excited-state photoreactions managed by a chiral hydrogen-bonding iridium sensitizer. J. Am. Chem. Soc. 139, 17186–17192 (2017).

    CAS 
    PubMed 
    PubMed Central 
    Article 

    Google Scholar
     

  • Bach, T., Bergmann, H. & Harms, Ok. Enantioselective intramolecular [2 + 2]-photocycloaddition reactions in answer. Angew. Chem. Int. Ed. 39, 2302–2304 (2000).

    CAS 
    Article 

    Google Scholar
     

  • Jon, S. Y. et al. A facile, stereoselective [2 + 2] photoreaction mediated by cucurbit [8] uril. Chem. Commun. 1938–1939 (2001).

  • Pattabiraman, M., Sivaguru, J. & Ramamurthy, V. Cucurbiturils as response containers for photocycloaddition of olefins. Isr. J. Chem. 58, 264–275 (2018).

    CAS 
    Article 

    Google Scholar
     

  • Barrow, S. J. et al. Cucurbituril-based molecular recognition. Chem. Rev. 115, 12320–12406 (2015).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Maddipatla, M. V. S. N. et al. Preorientation of olefins towards a single photodimer: cucurbituril-mediated photodimerization of protonated azastilbenes in water. Langmuir 23, 7545–7554 (2007).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Tanabe, J., Taura, D., Ousaka, N. & Yashima, E. Chiral template-directed regio-, diastereo-, and enantioselective photodimerization of an anthracene spinoff assisted by complementary amidinium–carboxylate salt bridge formation. J. Am. Chem. Soc. 139, 7388–7398 (2017).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Urushima, A. et al. Enantiodifferentiating photodimerization of a 2,6-disubstituted anthracene assisted by supramolecular double-helix formation with chiral amines. Angew. Chem. Int. Ed. 59, 7478–7486 (2020).

    CAS 
    Article 

    Google Scholar
     

  • Wei, X. et al. Reversal of regioselectivity throughout photodimerization of 2-anthracenecarboxylic acid in a water-soluble natural cavitand. Org. Lett. 21, 7868–7872 (2019).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Yoshizawa, M., Tamura, M. & Fujita, M. Diels–Alder in aqueous molecular hosts: uncommon regioselectivity and environment friendly catalysis. Science 312, 251–254 (2006).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Nishioka, Y., Yamaguchi, T., Kawano, M. & Fujita, M. Uneven [2 + 2] olefin cross photoaddition in a self-assembled host with distant chiral auxiliaries. J. Am. Chem. Soc. 130, 8160–8161 (2008).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Alagesan, M. et al. Enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylate mediated by a self-assembled iron tetrahedral coordination cage. J. Photochem. Photobiol. A 331, 95–101 (2016).

    CAS 
    Article 

    Google Scholar
     

  • Breslow, R. & Dong, S. D. Biomimetic reactions catalyzed by cyclodextrins and their derivatives. Chem. Rev. 98, 1997–2012 (1998).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Crini, G. Assessment: a historical past of cyclodextrins. Chem. Rev. 114, 10940–10975 (2014).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Szejtli, J. Introduction and common overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1754 (1998).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Rekharsky, M. V. & Inoue, Y. Complexation thermodynamics of cyclodextrins. Chem. Rev. 98, 1875–1918 (1998).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Hanessian, S., Benalil, A. & Laferriere, C. The synthesis of functionalized cyclodextrins as scaffolds and templates for molecular variety, catalysis, and inclusion phenomena. J. Org. Chem. 60, 4786–4797 (1995).

    CAS 
    Article 

    Google Scholar
     

  • Fukuhara, G. et al. Supramolecular photocyclodimerization of 2-hydroxyanthracene with a chiral hydrogen-bonding template, cyclodextrin and serum albumin. Photochem. Photobiol. Sci. 13, 162–171 (2014).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Rao, V. P. & Turro, N. J. Uneven induction in benzoin by photolysis of benzaldehyde adsorbed in cyclodextrin cavities. Tetrahedron Lett. 30, 4641–4644 (1989).

    CAS 
    Article 

    Google Scholar
     

  • Inoue, Y. et al. Inclusion-enhanced optical yield and E/Z ratio in enantiodifferentiating photoisomerization of cyclooctene included and sensitized by β-cyclodextrin monobenzoate. J. Am. Chem. Soc. 117, 11033–11034 (1995).

    CAS 
    Article 

    Google Scholar
     

  • Fukuhara, G., Mori, T., Wada, T. & Inoue, Y. Entropy-controlled supramolecular photochirogenesis: enantiodifferentiating Z–E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-β-cyclodextrin. Chem. Commun. 4199–4201 (2005).

  • Lu, R. et al. Supramolecular enantiodifferentiating photoisomerization of cyclooctene with modified beta-cyclodextrins: vital management by a bunch construction. Chem. Commun. 374–376 (2008).

  • Nakamura, A. & Inoue, Y. Supramolecular catalysis of the enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylate by γ-cyclodextrin. J. Am. Chem. Soc. 125, 966–972 (2003).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Nakamura, A. & Inoue, Y. Electrostatic manipulation of enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate inside γ-cyclodextrin cavity via chemical modification. Inverted product distribution and enhanced enantioselectivity. J. Am. Chem. Soc. 127, 5338–5339 (2005).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Yang, C. et al. Extremely Stereoselective photocyclodimerization of α-cyclodextrin-appended anthracene mediated by γ-cyclodextrin and cucurbit[8]uril: a dramatic steric impact working exterior the binding web site. J. Am. Chem. Soc. 130, 8574–8575 (2008).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Yang, C. et al. Twin supramolecular photochirogenesis: final stereocontrol of photocyclodimerization by a chiral scaffold and confining host. J. Am. Chem. Soc. 133, 13786–13789 (2011).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Koodanjeri, S., Pleasure, A. & Ramamurthy, V. Uneven induction with cyclodextrins: photocyclization of tropolone alkyl ethers. Tetrahedron 56, 7003–7009 (2000).

    CAS 
    Article 

    Google Scholar
     

  • Shailaja, J., Karthikeyan, S. & Ramamurthy, V. Cyclodextrin mediated solvent-free enantioselective photocyclization of N-alkyl pyridones. Tetrahedron Lett. 43, 9335–9339 (2002).

    CAS 
    Article 

    Google Scholar
     

  • Koodanjeri, S. & Ramamurthy, V. Cyclodextrin mediated enantio and diastereoselective geometric photoisomerization of diphenylcyclopropane and its derivatives. Tetrahedron Lett. 43, 9229–9232 (2002).

    CAS 
    Article 

    Google Scholar
     

  • Wada, T. et al. Bovine serum albumin-mediated enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate. J. Am. Chem. Soc. 125, 7492–7493 (2003).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Fuentealba, D. et al. Explaining the extremely enantiomeric photocyclodimerization of 2-anthracenecarboxylate certain to human serum albumin utilizing time-resolved anisotropy research. J. Am. Chem. Soc. 135, 203–209 (2013).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Nishijima, M. et al. Photochirogenesis with mutant human serum albumins: enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate. Chem. Commun. 49, 7433–7435 (2013).

    CAS 
    Article 

    Google Scholar
     

  • Ishida, Y. et al. Two-component liquid crystals as chiral response media: extremely enantioselective photodimerization of an anthracene spinoff pushed by the ordered microenvironment. Angew. Chem. Int. Ed. 47, 8241–8245 (2008).

    CAS 
    Article 

    Google Scholar
     

  • Ishida, Y. et al. Metastable liquid crystal as time-responsive response medium: aging-induced twin enantioselective management. J. Am. Chem. Soc. 135, 6407–6410 (2013).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Wei, X. et al. Enantioselective photoinduced cyclodimerization of a prochiral anthracene spinoff adsorbed on helical steel nanostructures. Nat. Chem. 12, 551–559 (2020).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Chen, X.-Y. et al. Selective photodimerization in a cyclodextrin steel–natural framework. J. Am. Chem. Soc. 143, 9129–9139 (2021).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Tamaki, T., Kokubu, T. & Ichimura, Ok. Regio- and stereoselective photodimerization of anthracene derivatives included by cyclodextrins. Tetrahedron 43, 1485–1494 (1987).

    CAS 
    Article 

    Google Scholar
     

  • Yang, C. et al. Stress and temperature-controlled enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylate mediated by secondary face- and skeleton-modified gamma-cyclodextrins. J. Org. Chem. 71, 3126–3136 (2006).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Yang, C., Mori, T. & Inoue, Y. Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by capped γ-cyclodextrins: vital management of enantioselectivity by cap rigidity. J. Org. Chem. 73, 5786–5794 (2008).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Ke, C. et al. Catalytic enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by a non-sensitizing chiral metallosupramolecular host. Angew. Chem. Int. Ed. 48, 6675–6677 (2009).

    CAS 
    Article 

    Google Scholar
     

  • Yang, C. et al. Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by γ-cyclodextrins with a versatile or inflexible cap. Org. Lett. 8, 3005–3008 (2006).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Vallavoju, N. & Sivaguru, J. Supramolecular photocatalysis: combining confinement and non-covalent interactions to regulate mild initiated reactions. Chem. Soc. Rev. 43, 4084–4101 (2014).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Welborn, V. V. & Head-Gordon, T. Electrostatics generated by a supramolecular capsule stabilizes the transition state for carbon–carbon reductive elimination from gold(III) advanced. J. Phys. Chem. Lett. 9, 3814–3818 (2018).

    Article 
    CAS 

    Google Scholar
     

  • Younger, T. A. et al. Rationalizing the exercise of an “synthetic diels-alderase”: establishing environment friendly and correct protocols for calculating supramolecular catalysis. J. Am. Chem. Soc. 142, 1300–1310 (2020).

    PubMed 
    Article 
    CAS 

    Google Scholar
     

  • Petroselli, M. et al. Radical reactions in cavitands unveil the results of affinity on dynamic supramolecular programs. J. Am. Chem. Soc. 142, 2396–2403 (2020).

    CAS 
    PubMed 
    Article 

    Google Scholar
     

  • Wei, X. et al. Enhanced irregular photodimers and switched enantioselectivity by solvent and temperature within the photocyclodimerization of 2-anthracenecarboxylate with modified β-cyclodextrins. J. Photochem. Photobiol. A 371, 374–381 (2019).

    CAS 
    Article 

    Google Scholar
     

  • Nishijima, M. et al. Excessive-sensitivity HPLC quantification of nonfluorescent however photolabile analyte via photoreversion in fluorescence detector. Chem. Lett. 39, 726–727 (2009).

    Article 
    CAS 

    Google Scholar
     

  • Bouas-Laurent, H. et al. Photodimerization of anthracenes in fluid answer: structural facets. Chem. Soc. Rev. 29, 43–55 (2000).

    CAS 
    Article 

    Google Scholar
     

  • Bouas-Laurent, H. et al. Photodimerization of anthracenes in fluid options: (half 2) mechanistic facets of the photocycloaddition and of the photochemical and thermal cleavage. Chem. Soc. Rev. 30, 248–263 (2001).

    CAS 
    Article 

    Google Scholar
     

  • Wang, Q. et al. Wavelength-controlled supramolecular photocyclodimerization of anthracenecarboxylate mediated by γ-cyclodextrins. Chem. Commun. 47, 6849–6851 (2011).

    CAS 
    Article 

    Google Scholar
     

  • RELATED ARTICLES

    LEAVE A REPLY

    Please enter your comment!
    Please enter your name here

    Most Popular

    Recent Comments