Control of chirality by cations in confined spaces: Photooxidation of enecarbamates inside zeolite supercages

Photochemistry and Photobiology

Volumn 82, Issue 1, 2006, Pages 123-131

  Sivaguru, J ^a   Saito, Hideaki ^a,b,c   Solomon, Marissa R ^a   Kaanumalle, Lakshmi S ^d   Poon, Thomas ^e   Jockusch, Steffen ^a   Adam, Waldemar ^f,g   Ramamurthy, V ^d   Inoue, Yoshihisa ^b,c   Turro, Nicholas J ^a,h  

^a Columbia University ^*  (United States)

^b OSAKA UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d Department of Biology   (United States)

^e KECK GRADUATE INSTITUTE   (United States)

^f UNIVERSITY OF WÜRZBURG   (Germany)

^g UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^h Mail Code 3119 ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33644775962     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/2005-06-15-RA-573     Document Type: Conference Paper

References (53)

1. Turro, N. J. (2000) From boiling stones to smart crystals: supramolecular and magnetic isotope control of radical-radical reactions in zeolites. Acc. Chem. Res. 33, 637-646.
2. Turro, N. J. (2002) Supramolecular organic photochemistry: control of covalent bond formation through noncovalent supramolecular interactions and magnetic effects. Proc. Natl. Acad. Sci. USA 99, 4805-4809.
3. Inoue, Y. and V. Ramamurthy (2004) Chiral Photochemistry. Marcel Dekker, New York.
4. Inoue, Y. (1992) Asymmetric photochemical reactions in solution. Chem. Rev. 92, 741-770.
5. Turro, N. J. and P. Wan (1985) Photolysis of dibenzyl ketones adsorbed on zeolite molecular sieves. Correlation of observed cage effects with carbonyl carbon-13 enrichment efficiencies. J. Am. Chem. Soc. 107, 678-682.
6. Turro, N. J., C. C. Cheng, L. Abrams and D. R. Corbin (1987) Size, shape, and site selectivities in the photochemical reactions of molecules adsorbed on pentasil zeolites. Effects of coadsorbed water. J. Am. Chem. Soc. 109, 2449-2456.
7. Ramamurthy, V., D. R. Corbin, N. J. Turro, Z. Zhang and M. A. Garcia Garibay (1991) Modification of photochemical reactivity by zeolites. A comparison between zeolite-solvent slurry and dry solid photolyses. J. Org. Chem. 56, 255-261.
8. Sivaguru, J., A. Natarajan, L. S. Kaanumalle, J. Shailaja, S. Uppili, A. Joy and V. Ramamurthy (2003) Asymmetric photoreactions within zeolites: role of confinement and alkali metal ions. Acc. Chem. Res. 36, 509-521.
9. Sivaguru, J., J. Shailaja, S. Uppili, K. Ponchot, A. Joy, N. Arunkumar and V. Ramamurthy (2002) Achieving enantio and diastereoselectivities in photoreactions through the use of a confined space. In Organic Solid-State Reactions (Edited by F. Toda), pp 159-188. Kluwer Academic Press, Dordrecht, the Netherlands.
10. Adam, W., S. G. Bosio and N. J. Turro (2002) Control of the mode selectivity (ene reaction versus [2 + 2] cycloaddition) in the photooxygenation of ene carbamates: directing effect of an alkenylic nitrogen functionality. J. Am. Chem. Soc. 124, 14004-14005.
11. Adam, W., S. G. Bosio and N. J. Turro (2002) Highly diastereoselective dioxetane formation in the photooxygenation of enecarbamates with an oxazolidinone chiral auxiliary: steric control in the [2 + 2] cycloaddition of singlet oxygen through conformational alignment. J. Am. Chem. Soc. 124, 8814-8815.
12. Adam, W., S. G. Bosio, N. J. Turro and B. T. Wolff (2004) Enecarbamates as selective substrates in oxidations: chiral-auxiliary-controlled mode selectivity and diastereoselectivity in the [2+2] cycloaddition and ene reaction of singlet oxygen and in the epioxidation by DMD and mCPBA. J. Org. Chem. 69, 1704-1715.
13. Breck, D. W. (1991) Zeolite Molecular Sieves. Chemistry and Use. John Wiley & Sons, New York.
14. Dyer, A. (1988) An Introduction to Zeolite Molecular Sieves. John Wiley & Sons, New York.
15. Szostak, R. (1992) Handbook of Molecular Sieves. Van Nostrand Reinhold, New York.
16. Ramamurthy, V. (1991) Photoprocesses of organic molecules included in zeolites. In Photochemistry in Organized and Confined Media (Edited by V. Ramamurthy), Wiley-VCH, New York.
17. Grey, C. P., F. I. Poshni, A. F. Gualtieri, P. Norby, J. C. Hanson and D. R. Corbin (1997) Combined MAS NMR and X-ray powder diffraction structural characterization of hydrofluorocarbon-134 adsorbed on zeolite NaY: observation of cation migration and strong sorbate-cation interactions. J. Am. Chem. Soc. 119, 1981-1989.
18. David, H. O. (1995) The crystal structure of dehydrated NaX. Zeolites 15, 439-443.
19. Kirschhock, C. and H. Fuess (1996) m-Dinitrobenzene in zeolite NaY: four different arrangements. Zeolites 17, 381-388.
20. Lim, K. H. and C. P. Grey (2000) Characterization of extra-framework cation positions in zeolites NaX and NaY with very fast 23Na MAS and multiple quantum MAS NMR spectroscopy. J. Am. Chem. Soc. 122, 9768-9780.
21. Lim, K. H., F. Jousse, S. M. Auerbach and C. P. Grey (2001) Double resonance NMR and molecular simulations of hydrofluorocarbon binding on Faujasite zeolites NaX and NaY: the importance of hydrogen bonding in controlling adsorption geometries. J. Phys. Chem. B. 105, 9918-9929.
22. Jaramillo, E., C. P. Grey and S. M. Auerbach (2001) Molecular dynamics studies of hydrofluorocarbons in Faujasite-type zeolites: modeling guest-induced cation migration in dry zeolites. J. Phys. Chem. B. 105, 12319-12329.
23. Norby, P., F. I. Poshni, A. F. Gualtieri, J. C. Hanson and C. P. Grey (1998) Cation migration in zeolites: an in situ powder diffraction and MAS NMR study of the structure of zeolite Cs(Na)-Y during dehydration. J. Phys. Chem. B. 102, 839-856.
24. Ramamurthy, V., D. R. Sanderson and D. F. Eaton (1993) Control of dye assembly within zeolites: role of water. J. Am. Chem. Soc. 115, 10438-10439.
25. Shailaja, J., J. Sivaguru, R. J. Robbins, V. Ramamurthy, R. B. Sunoj and J. Chandrasekhar (2000) Singlet oxygen mediated oxidation of olefins within zeolites: selectivity and complexities. Tetrahedron 56, 6927-6943.
26. Li, X. and V. Ramamurthy (1996) Selective oxidation of olefins within organic dye cation exchanged zeolites. J. Am. Chem. Soc. 118, 10666-10667.
27. Zhou, W. and E. L. Clennan (1999) Organic reactions in zeolites. 1. Photooxidations of sulfides in methylene blue doped zeolite Y. J. Am. Chem. Soc. 121, 2915-2916.
28. Clennan, E. L. and J. P. Sram (2000) Photochemical reactions in the interior of a zeolite. Part 5: the origin of the zeolite induced regioselectivity in the singlet oxygen ene reaction. Tetrahedron 56, 6945-6950.
29. Stratakis, M., D. Kalaitzakis, D. Stavroulakis, G. Kosmas and C. Tsangarakis (2003) Remarkable change of the diastereoselection in the dye-sensitized ene hydroperoxidation of chiral alkenes by zeolite confinement. Org. Lett. 5, 3471-3474.
30. Stratakis, M. and G. Froudakis (2000) Site specificity in the photooxidation of some trisubstituted alkenes in thionin-supported zeolite Na-Y. On the role of the alkali metal cation. Org. Lett. 2, 1369-1372.
31. Foote, C. S. (1968) Photosensitized oxygenations and the role of singlet oxygen. Acc. Chem. Res. 1, 104-110.
32. Frimer, A. A. (1965) Singlet Oxygen Part I-IV. Boca Raton, FL.
33. Gollnick, K. and H. J. Kuhn (1979) Ene-reactions with singlet oxygen. In Singlet Oxygen (Edited by H. H. Wasserman and R. W. Murray), pp. 287-427. Academic Press, New York.
34. Wasserman, H. H. and R. W. Murray (1979) Singlet Oxygen. Academic Press, New York.
35. Sivaguru, J., T. Poon, R. Franz, S. Jockusch, W. Adam and N. J. Turro (2004) Stereocontrol within confined spaces: enantioselective photooxidation of enecarbamates inside zeolite supercages. J. Am. Chem. Soc. 126, 10816-10817.
36. Poon, T., J. Sivaguru, R. Franz, S. Jockusch, C. Martinez, I. Washington, W. Adam, Y. Inoue and N. J. Turro (2004) Temperature and solvent control of the stereoselectivity in the reactions of singlet oxygen with oxazolidinone- substituted enecarbamates. J. Am. Chem. Soc. 126, 10498-10499.
37. Sivaguru, J., R. B. Sunoj, T. Wada, Y. Origane, Y. Inoue and V. Ramamurthy (2004) Enhanced eiastereoselectivity via confinement: photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites. J. Org. Chem. 69, 6533-6547.
38. Sivaguru, J., R. B. Sunoj, T. Wada, Y. Origane, Y. Inoue and V. Ramamurthy (2004) Enhanced diastereoselectivity via confinement: diastereoselective photoisomerization of 2,3-diphenyl-1-benzoylcyclopropane derivatives within zeolites. J. Org. Chem. 69, 5528-5536.
39. Jockusch, S., J. Sivaguru, N. J. Turro and V. Ramamurthy (2005) Direct measurement of the singlet oxygen lifetime in zeolites by near-IR phosphorescence. Photochem. Photobiol. Sci. 4, 403-405.
40. Frisch, M. J., G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. J. A. Montgomery, T. K. Vreven, K. N., J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople (1998) Gaussian 98, Revision A.11; Gaussian, Inc., Pittsburgh, PA.
41. Poon, T., J. Turro Nicholas, J. Chapman, P. Lakshminarasimhan, X. Lei, W. Adam and G. Bosio Sara (2003) A supramolecular "ship in bottle" strategy for enantiomeric selectivity in geminate radical pair recombination. Org. Lett. 5, 2025-2028.
42. Ramamurthy, V., D. R. Corbin, D. F. Eaton and N. J. Turro (1989) Modification of photochemical reactivity by zeolites: role of cations in controlling the behavior of radicals generated within faujasites. Tetrahedron Lett. 30, 5833-5836.
43. Ramamurthy, V., D. R. Corbin, N. J. Turro and Y. Sato (1989) Modification of photochemical reactivity by zeolites: cation enhanced a-cleavage of aryl alkyl ketones included in faujasites. Tetrahedron Lett. 30, 5829-5832.
44. Raber, D. J., N. K. Raber, J. Chandrasekhar and P. v. R. Schleyer (1984) Geometries and energies of complexes between formaldehyde and first- and second-row cations. A theoretical study. Inorg. Chem. 23, 4076-4080.
45. Ma, J. C. and D. A. Dougherty (1997) The cation-π interaction. Chem. Rev. 97, 1303-1324.
46. Dunbar, R. C. (2000) Complexation of Na+ and K+ to aromatic amino acids: a density functional computational study of cation-π interactions. J. Phys. Chem. A 104, 8067-8074.
47. Hoyau, S. and G. Ohanessian (1998) Interaction of alkali metal cations (Li+-Cs+) with glycine in the gas phase: a theoretical study. Chem. Eur. J. 4, 1561-1569.
48. Jockusch, R. A., A. S. Lemoff and E. R. William (2001) Effect of metal ion and water coordination on the structure of a gas-phase amino acid. J. Am. Chem. Soc. 123, 12255-12265.
49. Jockusch, R. A., W. D. Price and E. R. Williams (1999) Structure of cationized arginine (Arg·M+, M = H, Li, Na, K, Rb, and Cs) in the gas phase: further evidence for zwitterionic arginine. J. Phys. Chem. A 103, 9266-9274.
50. Siu, F. M., N. L. Ma and C. W. Tsang (2001) Cation-π interactions in sodiated phenylalanine complexes: is phenylalanine in the charge-solvated or zwitterionic form? J. Am. Chem. Soc. 123, 3397-3398.
51. Wyttenbach, T., M. Witt and M. T. Bowers (2000) On the stability of amino acid zwitterions in the gas phase: the influence of derivatization, proton affinity, and alkali ion addition. J. Am. Chem. Soc. 122, 3458-3464.
52. Poon, T., N. J. Turro, J. Chapman, P. Lakshminarasimhan, X. Lei, S. Jockusch, R. Franz, I. Washington, W. Adam and S. G. Bosio (2003) Stereochemical features of the physical and chemical interactions of singlet oxygen with enecarbamates. Org. Lett. 5, 4951-4953.
53. Sivaguru, J., H. Saito, T. Poon, T. Omonuwa, R. Franz, S. Jockusch, C. Hooper, Y. Inoue, W. Adam and N. J. Turro (2005) Stereoselective photooxidation of enecarbamates: reactivity of ozone vs singlet oxygen. Org. Lett. 7, 2089-2092.