Regio- and stereoselectivity in the Paternò-Büchi reaction on furan derivatives

International Journal of Photoenergy

Volumn 2006, Issue , 2006, Pages

  D'Auria, Maurizio ^a   Emanuele, Lucia ^a   Racioppi, Rocco ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746902427     PISSN: 1110662X     EISSN: 1110662X     Source Type: Journal    
DOI: 10.1155/IJP/2006/84645     Document Type: Article

References (44)

1. T. Bach Stereoselective intermolecular [2 + 2] -photocycloaddition reactions and their application in synthesis. Synthesis 5 1998 683 703
2. E. Paternò G. Chieffi Gazzetta Chimica Italiana Sintesi in chimica organica per mezzo della luce. Nota II. Composti degli idrocarburi non saturi con aldeidi e chetoni. 39 1909 341
3. G. Büchi C. G. Inman E. S. Lipinsky Light-catalyzed organic reactions. I. The reaction of carbonyl compounds with 2-methyl-2-butene in the presence of ultraviolet light. Journal of the American Chemical Society 76 1954 17 4327 4331
4. G. Ciamician The photochemistry of the future. Science 36 1912 385 394
5. I. J. Palmer I. N. Ragazos F. Bernardi M. Olivucci M. A. Robb An MC-SCF study of the (photochemical) Paternò-Büchi reaction. Journal of the American Chemical Society 116 5 1994 2121 2132
6. S. C. Freilich K. S. Peters Observation of the 1,4 biradical in the Paternò-Büchi reaction. Journal of the American Chemical Society 103 1981 20 6255 6257
7. S. C. Freilich K. S. Peters Picosecond dynamics of the Paternò-Büchi reaction. Journal of the American Chemical Society 107 1985 13 3819 3822
8. A. G. Kutateladze Conformational analysis of singlet-triplet state mixing in Paternò-Büchi diradicals. Journal of the American Chemical Society 123 38 2001 9279 9282
9. M. D'Auria L. Emanuele R. Racioppi G. Romaniello The Paternò- Büchi reaction on furan derivatives. Current Organic Chemistry 7 14 2003 1443 1459
10. M. D'Auria L. Emanuele R. Racioppi D. C. Neckers W. S. Jenks T. Wolff 1, 2-Cycloaddition reaction of carbonyl compounds and pentaatomic heterocyclic compounds. Advances in Photochemistry 28 John Wiley & Sons Hoboken, NJ, USA 2005 81 127
11. H. Buschmann H.-D. Scharf N. Hoffmann P. Esser The isoinversion principle - a general model of chemical selectivity. Angewandte Chemie - International Edition in English 30 5 1991 477 515
12. A. G. Griesbeck S. Buhr M. Fiege H. Schmickler J. Lex Stereoselectivity of triplet photocycloadditions:1 diene-carbonyl reactions and solvent effects. Journal of Organic Chemistry 63 12 1998 3847 3854
13. M. Abe abe@ap.chem.eng.osaka-u.ac.jp T. Kawakami S. Ohata K. Nozaki M. Nojima Mechanism of stereo- and regioselectivity in the Paternò- Büchi reaction of furan derivatives with aromatic carbonyl compounds: importance of the conformational distribution in the intermediary triplet 1,4-diradicals. Journal of the American Chemical Society 126 9 2004 2838 2846
14. A. G. Griesbeck M. Abe abe@ap.chem.eng.osaka-u.ac.jp S. Bondock Selectivity control in electron spin inversion processes: regio- and stereochemistry of Paternò-Büchi photocycloadditions as a powerful tool for mapping intersystem crossing processes. Accounts of Chemical Research 37 12 2004 919 928
15. M. D'Auria O. A. Attanasi D. Spinelli Paternò-Büchi reaction on furan: regio- and stereochemistry. Targets in Heterocyclic Systems, Chemistry and Properties 7 Italian Society of Chemistry Rome, Italy 2003 157 173
16. M. Ogata H. Watanabe H. Kano Tetrahedron Letters Photochemical cycloaddition of benzophenone to furans. 1967 533
17. H. A. J. Carless D. J. Haywood Photochemical syntheses of 2,6-dioxabicyclo [3.2.0] heptanes. Journal of the Chemical Society, Chemical Communications 1980 22 1067 1068
18. A. G. Griesbeck S. Stadtmüller Photocycloaddition of benzaldehyde to cyclic olefins: electronic control of endo stereoselectivity. Journal of the American Chemical Society 112 3 1990 1281 1283
19. A. G. Griesbeck S. Stadtmüller Electronic control of stereoselectivity in photocycloaddition reactions. 4. Effects of methyl substituents at the donor olefin. Journal of the American Chemical Society 113 1991 18 6923 6928
20. A. G. Griesbeck S. Stadtmüller Regio-und Stereoselektive Photocycloadditionen Aromatischer Aldehyde an Furan und 2,3-Dihydrofuran. Chemische Berichte 123 1990 357 362
21. G. O. Schenck R. Hartman R. Steinmetz Vierringsynthesen durch photosensibilisierte cycloaddition von dimethylmaleinsäurenhydrid an olefine. Chemische Berichte 96 1963 498
22. D. Gagnaire E. Payo-Subiza Bulletin de Société Chimique de France Couplage des protons d'un méthyle ̀ travers cinq liaisons en resonance magnétique nucléaire: ethers vinyliques hétérocycliques. 1963 2623
23. S. Toki K. Shima H. Sakurai Organic photochemical reactions. I. The synthesis of substituted oxetanes by the photoaddition of aldehydes to furans. Bulletin of the Chemical Society of Japan 38 1965 5 760 762
24. T. Nakano C. Rivas C. Perez K. Tori Configuration and stereochemistry of photoproducts by application of the nuclear Overhauser effect. Adducts of benzophenone with methyl-substituted furans and 2,5-dimethylthiophen, and of methyl-substituted maleic anhydrides with thiophen and its methyl derivatives, and benzo-[b]thiophen. Journal of the Chemical Society, Perkin Transactions 1 1973 2322 2327
25. E. B. Whipple G. R. Evanega The assignment of configuration to the photoaddition products of unsymmetrical carbonyls to furan using pseudocontact shifts. Tetrahedron 24 1968 3 1299 1310
26. M. D'Auria L. Emanuele R. Racioppi On the Paternò-Büchi reaction of chiral phenylglyoxylate esters with furan derivatives. Photochemical and Photobiological Sciences 2 9 2003 904 913
27. M. D'Auria L. Emanuele R. Racioppi Diastereoselectivity in the Paternò-Büchi reaction on furan derivatives. Tetrahedron Letters 45 20 2004 3877 3880
28. M. D'Auria L. Emanuele V. Pace R. Racioppi Diastereoselective Paternò-Büchi reaction on furan derivatives-reaction with asymmetric ketones. Letters in Organic Chemistry 3 2006 244 246 5
29. W. Adam adam@chemie.uni-wuerzburg.de K. S. Peters E. M. Peters V. R. Stegmann Hydroxy-directed regio- and diastereoselective [2+2] photocycloaddition (Paternò-Büchi reaction) of benzophenone to chiral allylic alcohols. Journal of the American Chemical Society 122 12 2000 2958 2959
30. W. Adam V. R. Stegmann Hydroxy-group directivity in the regioselective and diastereoselective [2+2] photocycloaddition (Paternò-Büchi reaction) of aromatic carbonyl compounds to chiral and achiral allylic substrates: the preparation of oxetanes with up to three stereogenic centers as synthetic building blocks. Synthesis 8 2001 1203 1214
31. M. Prein W. Adam adam@vax.rz.uni-wuerzburg.d400.de The schenck ene reaction: diastereoselective oxyfunctionalization with singlet oxygen in synthetic applications. Angewandte Chemie - International Edition 35 5 1996 477 494
32. A. G. Griesbeck S. Bondock Paternò-Büchi reactions of allylic alcohols and acetates with aldehydes: hydrogen-bond interaction in the excited singlet and triplet states? Journal of the American Chemical Society 123 25 2001 6191 6192
33. T. Bach J. Schröder K. Harms Diastereoselective photocycloaddition of an axial chiral enamide. Tetrahedron Letters 40 51 1999 9003 9004
34. T. Bach H. Bergmann K. Harms High facial diastereoselectivity in the photocycloaddition of a chiral aromatic aldehyde and an enamide induced by intermolecular hydrogen bonding. Journal of the American Chemical Society 121 45 1999 10650 10651
35. A. Yokoyama K. Mizuno Stereoselective photocycloaddition of alkenes to naphthalene rings assisted by hydrogen bonding. Organic Letters 2 2000 22 3457 3459
36. T. Bach The Paternò-Büchi reaction of 3-heteroatom- substituted alkenes as a stereoselective entry to polyfunctional cyclic and acyclic molecules. Liebigs Annalen 1997 1997 8 1627 1634
37. M. D'Auria R. Racioppi G. Romaniello The Paternò-Büchi reaction of 2-furylmethanols. European Journal of Organic Chemistry 19 2000 3265 3272
38. M. D'Auria R. Racioppi Paternò-Büchi reaction on 5-methyl-2-furylmethanol derivatives. Arkivoc 2, part II 2000 133 140
39. M. D'Auria L. Emanuele G. Poggi R. Racioppi G. Romaniello On the stereoselectivity of the Paternò-Büchi reaction between carbonyl compounds and 2-furylmethanol derivatives. The case of aliphatic aldehydes and ketones. Tetrahedron 58 25 2002 5045 5051
40. M. D'Auria L. Emanuele R. Racioppi The stereoselectivity of the Paternò-Büchi reaction between tertiary 2-furylmethanol derivatives and aromatic carbonyl compounds: on the nature of the hydroxy directing effect. Photochemical and Photobiological Sciences 3 10 2004 927 932
41. M. D'Auria L. Emanuele R. Racioppi Stereoselectivity in the Paternò-Büchi reaction on chiral allylic alcohols, for a discussion of the hydroxy directing effect. Letters in Organic Chemistry 2 2005 2 132 135
42. K. Shima H. Sakurai Organic photochemical reactions. IV. Photoaddition reactions of various carbonyl compounds to furan. Bulletin of the Chemical Society of Japan 39 1966 8 1806 1808
43. T. S. Cantrell A. C. Allen H. Ziffer Photochemical 2 + 2 cycloaddition of arenecarboxylic acid esters to furans and 1,3-dienes. 2 + 2 Cycloreversion of oxetanes to dienol esters and ketones. Journal of Organic Chemistry 54 1989 1 140 145
44. C. Rivas R. A. Bolivar M. Cucarella Journal of Heterocyclic Chemistry Photoaddition of carbonyl compounds to five-membered ring heterocycles. 19 1982 529