Synthesis of fluorinated tricyclic scaffolds by intramolecular [2+2] photocycloaddition reactions

Angewandte Chemie - International Edition

Volumn 51, Issue 40, 2012, Pages 10169-10172

  Fort, Diego A ^a   Woltering, Thomas J ^b   Nettekoven, Matthias ^b   Knust, Henner ^b   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

cycloaddition; diastereoselectivity; fluorine; photochemistry; strained molecules

Indexed keywords

DIASTEREO-SELECTIVITY; ELECTRON-DEFICIENT; FLUORINATED PRODUCTS; IRRADIATION CONDITIONS; PHOTOCYCLOADDITION; PHOTOCYCLOADDITION REACTION; SIDE-CHAINS; STRAINED MOLECULES;

CYCLOADDITION; FLUORINE; PHOTOCHEMICAL REACTIONS;

SCAFFOLDS;

EID: 84866998648     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201204080     Document Type: Article

References (56)

1. T. Hiyama, Organofluorine Compounds, Springer, Berlin, 2010
2. D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308-319
3. K. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, 2006
4. P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis Reactivity, Applications, Wiley-VCH, Weinheim, 2004.
5. F. M. D. Ismail, J. Fluorine Chem. 2002, 118, 27-33
6. H.-J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 2004, 5, 637-643
7. J. P. Bégué, D. Bonnet-Delpon, J. Fluorine Chem. 2006, 127, 992-1012
8. K. L. Kirk, J. Fluorine Chem. 2006, 127, 1013-1029
9. C. Isanbor, D. O'Hagan, J. Fluorine Chem. 2006, 127, 303-319
10. W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369
11. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330
12. A. K. Podichetty, S. Wagner, S. Schröer, A. Faust, O. Schober, M. Schäfers, K. Kopka, G. Haufe, J. Med. Chem. 2009, 52, 3484-3495.
13. Fluorinated Heterocyclic Compounds (Ed.:, V. A. Petrov,), Wiley, Hoboken, 2009
14. S. Fustero, J. F. Sanz-Cervera, J. L. Aceña, M. Sánchez-Rosellõ, Synlett 2009, 525-549
15. L. E. Zimmer, C. Sparr, R. Gilmour, Angew. Chem. 2011, 123, 12062-12074
16. Angew. Chem. Int. Ed. 2011, 50, 11860-11871.
17. J. P. Hehn, C. Müller, T. Bach, in Handbook of Synthetic Photochemistry (Eds.:, A. Albini, M. Fagnoni,), Wiley-VCH, Weinheim, 2009, pp. 171-215
18. S. A. Fleming, in Molecular and Supramolecular Photochemistry, Vol. 12 (Eds.:, A. G. Griesbeck, J. Mattay,), Marcel Dekker, New York, 2005, pp. 141-160
19. P. Margaretha, in Molecular and Supramolecular Photochemistry, Vol. 12 (Eds.:, A. G. Griesbeck, J. Mattay,), Marcel Dekker, New York, 2005, pp. 211-237
20. nd ed., (Eds.: W. Horspool, F. Lenci,), CRC, Boca Raton, 2004, pp. 71 /1- 71 /14
21. T. Bach, Synthesis 1998, 683-703
22. J.-P. Pete, Adv. Photochem. 1996, 21, 135-216
23. J. Mattay, R. Conrads, R. Hoffmann, in Methoden der Organischen Chemie (Houben-Weyl) 4te Aufl., Band E 21c (Eds.:, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann,), Thieme, Stuttgart, 1995, pp. 3085-3132
24. M. T. Crimmins, T. L. Reinhold, Org. React. 1993, 44, 297-588.
25. W. P. Dailey, D. M. Lemal, J. Am. Chem. Soc. 1984, 106, 1169-1170
26. R. A. Correa, N. Jing, J. Org. Chem. 1993, 58, 6406-6409.
27. H. Kimoto, K. Takahashi, H. Muramatsu, Bull. Chem. Soc. Jpn. 1980, 53, 764-769
28. D. Andrew, D. J. Hastings, A. C. Weedon, J. Am. Chem. Soc. 1994, 116, 10870-10882.
29. A. J. Wexler, J. S. Swenton, J. Am. Chem. Soc. 1976, 98, 1602-1604
30. A. J. Wexler, R. J. Balchunis, J. S. Swenton, J. Org. Chem. 1984, 49, 2733-2738
31. T. Iwaoka, N. Katagiri, M. Sato, C. Kaneko, Chem. Pharm. Bull. 1992, 40, 2319-2324
32. C. Gauzy, B. Saby, E. Pereira, S. Faure, D. J. Aitken, Synlett 2006, 1394-1398.
33. A. N. Tkachenko, D. S. Radchenko, P. K. Mykhailiuk, O. O. Grygorenko, I. V. Komarov, Org. Lett. 2009, 11, 5674-5676.
34. M. Kemmler, T. Bach, Angew. Chem. 2003, 115, 4973-4975
35. Angew. Chem. Int. Ed. 2003, 42, 4824-4826
36. M. Kemmler, T. Bach, Eur. J. Org. Chem. 2004, 4582-4595
37. M. Fleck, C. Yang, T. Wada, Y. Inoue, T. Bach, Chem. Commun. 2007, 822-824
38. M. Fleck, T. Bach, Chem. Eur. J. 2010, 16, 6015-6032
39. J. P. Hehn, D. Gamba-Sánchez, M. Kemmler, M. Fleck, B. Basler, T. Bach, Synthesis 2010, 2308-2312
40. R. Weixler, J. P. Hehn, T. Bach, J. Org. Chem. 2011, 76, 5924-5935.
41. M. M. Kremlev, I. S. Mazny, Y. L. Yagupolskii, J. Fluorine Chem. 1991, 54, 100
42. T. I. Gorbunova, A. Y. Zapevalov, V. I. Saloutin, Russ. Chem. Bull. 1995, 44, 1470-1473
43. A. Arnone, D. D. DesMareau, B. Novo, V. A. Petrov, M. Pregnolato, G. Resnati, J. Org. Chem. 1996, 61, 8805-8810.
44. Y. Tada, M. Sato, N. Takeno, Y. Nakacho, K. Shigehara, Makromol. Chem. 1993, 194, 2163-2171.
45. W. R. Li, S. T. Lin, N.-M. Hsu, M. S. Chern, J. Org. Chem. 2002, 67, 4702-4706.
46. G. R. Waitkins, C. W. Clark, Chem. Rev. 1945, 36, 235-289.
47. D. I. Schuster, G. N. Lem, A. Kaprinidis, Chem. Rev. 1993, 93, 3-22.
48. H. Meerwein, R. Schmidt, Justus Liebigs Ann. Chem. 1925, 444, 221-238
49. A. Verley, Bull. Soc. Chim. Fr. 1925, 37, 537
50. W. Ponndorf, Angew. Chem. 1926, 39, 138-143
51. J. Yin, M. A. Huffman, K. M. Conrad, J. D. Armstrong III, J. Org. Chem. 1996, 61, 8805-8810.
52. S. Jarosz, A. Zamojski, Tetrahedron 1982, 38, 1453-1456
53. S. L. Schreiber, Science 1985, 227, 857-863
54. C. Žagar, H.-D. Scharf, Chem. Ber. 1991, 124, 967-969.
55. A. G. O'Brien, Tetrahedron 2011, 67, 9639-9667
56. A. Mengel, O. Reiser, Chem. Rev. 1999, 99, 1191-1223.