Synthetic applications of photoinduced electron transfer decarboxylation reactions

Synlett

Volumn , Issue 7, 1999, Pages 1169-1178

  Griesbeck, Axel G ^a   Kramer, Wolfgang ^a   Oelgemöller, Michael ^a  

^a Inst fur Organische Chem der U   (Germany)

Author keywords

Alkali metal carboxylates; Chirality memory; Macrocyclization; Photodecarboxylation; Phthalimides; keto carboxylates

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; INDOLIZIDINE DERIVATIVE; MALEIC ACID; PHTHALIC ACID; PYRROLIZIDINE DERIVATIVE; QUINOLINIC ACID; TRIMELLITIC ANHYDRIDE;

CHIRALITY; CONTROLLED STUDY; CYCLIZATION; DECARBOXYLATION; ELECTRON TRANSPORT; MOLECULAR INTERACTION; PHOTOACTIVATION; REVIEW; SYNTHESIS;

EID: 0032814028     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3159     Document Type: Review

References (55)

1. Curran, P. D.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, New York 1996. Regitz, M.; Giese, B. (Eds.) Methods Org. Chem. (Houben-Weyl) 1989, E 19a. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: Oxford 1986.
2. Curran, P. D.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, New York 1996. Regitz, M.; Giese, B. (Eds.) Methods Org. Chem. (Houben-Weyl) 1989, E 19a. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: Oxford 1986.
3. Curran, P. D.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, New York 1996. Regitz, M.; Giese, B. (Eds.) Methods Org. Chem. (Houben-Weyl) 1989, E 19a. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press: Oxford 1986.
4. Kavarnos, G. J. Fundamentals of Photoinduced Electron Transfer, VCH: Weinheim, New York 1993.
5. Fox, M. A.; Chanon, M. (Eds.) Photoinduced Electron Transfer Part A-D, Elsevier: Amsterdam 1988. Mattay, J. (Ed.) Topics in Current Chemistry 1990, 156; 1990, 158 1991, 159 1992, 163 1993, 168.
6. Fox, M. A.; Chanon, M. (Eds.) Photoinduced Electron Transfer Part A-D, Elsevier: Amsterdam 1988. Mattay, J. (Ed.) Topics in Current Chemistry 1990, 156; 1990, 158 1991, 159 1992, 163 1993, 168.
7. Fox, M. A.; Chanon, M. (Eds.) Photoinduced Electron Transfer Part A-D, Elsevier: Amsterdam 1988. Mattay, J. (Ed.) Topics in Current Chemistry 1990, 156; 1990, 158 1991, 159 1992, 163 1993, 168.
8. Fox, M. A.; Chanon, M. (Eds.) Photoinduced Electron Transfer Part A-D, Elsevier: Amsterdam 1988. Mattay, J. (Ed.) Topics in Current Chemistry 1990, 156; 1990, 158 1991, 159 1992, 163 1993, 168.
9. Fox, M. A.; Chanon, M. (Eds.) Photoinduced Electron Transfer Part A-D, Elsevier: Amsterdam 1988. Mattay, J. (Ed.) Topics in Current Chemistry 1990, 156; 1990, 158 1991, 159 1992, 163 1993, 168.
10. Fox, M. A.; Chanon, M. (Eds.) Photoinduced Electron Transfer Part A-D, Elsevier: Amsterdam 1988. Mattay, J. (Ed.) Topics in Current Chemistry 1990, 156; 1990, 158 1991, 159 1992, 163 1993, 168.
11. Griesbeck, A, G.; Henz, A.; Hirt, J. Synthesis 1996, 1261.
12. Griesbeck, A. G.; Mauder, H.; Müller, I.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Tetrahedron Lett. 1993, 34, 453. Griesbeck, A. G.; Hirt, J.; Peters, K.; Peters, E.-M., von Schnering, H. G. Chem. Eur. J. 1996, 2, 1388. Griesbeck, A. G.; Hirt, J.; Kramer, W.; Dallakian, P. Tetrahedron 1998, 54, 3169.
13. Griesbeck, A. G.; Mauder, H.; Müller, I.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Tetrahedron Lett. 1993, 34, 453. Griesbeck, A. G.; Hirt, J.; Peters, K.; Peters, E.-M., von Schnering, H. G. Chem. Eur. J. 1996, 2, 1388. Griesbeck, A. G.; Hirt, J.; Kramer, W.; Dallakian, P. Tetrahedron 1998, 54, 3169.
14. Griesbeck, A. G.; Mauder, H.; Müller, I.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Tetrahedron Lett. 1993, 34, 453. Griesbeck, A. G.; Hirt, J.; Peters, K.; Peters, E.-M., von Schnering, H. G. Chem. Eur. J. 1996, 2, 1388. Griesbeck, A. G.; Hirt, J.; Kramer, W.; Dallakian, P. Tetrahedron 1998, 54, 3169.
15. Griesbeck, A. G.; Buhr, S.; Fiege, M.; Schmickler, H.; Lex, J. J. Org. Chem. 1998, 63, 3847.
16. Griesbeck, A. G.; Henz, A.; Hirt, J.; Ptatschek, V.; Engel, T.; Löffler, D.; Schneider, F. W. Tetrahedron 1994, 50, 701.
17. Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
18. Quinckert, G. Angew. Chem. 1975, 87, 851; Angew. Chem. Int. Ed. Engl. 1975, 14, 790.
19. Quinckert, G. Angew. Chem. 1975, 87, 851; Angew. Chem. Int. Ed. Engl. 1975, 14, 790.
20. Griesbeck, A. G., Mauder, H., Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70.
21. Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. Coyle, J. D., in Synthetic Organic Photochemistry, Horspool, W. M. (Ed.) Plenum Press: New York 1984, 259. Mazzocchi, P. H. Org. Photochem. 1981, 5, 421. Griesbeck, A. G.; Mauder, H. in Handbook of Organic Photochemistry and Photobiology, Horspool, W. M.; Song, P.-S. (Eds.) CRC Press: Boca Raton 1995, 513.
22. Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. Coyle, J. D., in Synthetic Organic Photochemistry, Horspool, W. M. (Ed.) Plenum Press: New York 1984, 259. Mazzocchi, P. H. Org. Photochem. 1981, 5, 421. Griesbeck, A. G.; Mauder, H. in Handbook of Organic Photochemistry and Photobiology, Horspool, W. M.; Song, P.-S. (Eds.) CRC Press: Boca Raton 1995, 513.
23. Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. Coyle, J. D., in Synthetic Organic Photochemistry, Horspool, W. M. (Ed.) Plenum Press: New York 1984, 259. Mazzocchi, P. H. Org. Photochem. 1981, 5, 421. Griesbeck, A. G.; Mauder, H. in Handbook of Organic Photochemistry and Photobiology, Horspool, W. M.; Song, P.-S. (Eds.) CRC Press: Boca Raton 1995, 513.
24. Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. Coyle, J. D., in Synthetic Organic Photochemistry, Horspool, W. M. (Ed.) Plenum Press: New York 1984, 259. Mazzocchi, P. H. Org. Photochem. 1981, 5, 421. Griesbeck, A. G.; Mauder, H. in Handbook of Organic Photochemistry and Photobiology, Horspool, W. M.; Song, P.-S. (Eds.) CRC Press: Boca Raton 1995, 513.
25. Wintgens, V.; Valat, P.; Kossanyi, J.; Biczok, L.; Demeter, A.; Bérces, T. J. Chem. Soc. Faraday Trans. 1994, 90, 411. Görner, H.; Griesbeck, A. G. J. Photochem. Photobiol. A: Chem, submitted.
26. Wintgens, V.; Valat, P.; Kossanyi, J.; Biczok, L.; Demeter, A.; Bérces, T. J. Chem. Soc. Faraday Trans. 1994, 90, 411. Görner, H.; Griesbeck, A. G. J. Photochem. Photobiol. A: Chem, submitted.
27. Griesbeck, A. G. Liebigs Ann. 1996, 1951-1958. Griesbeck, A. G. Chimia 1998, 52, 272.
28. Griesbeck, A. G. Liebigs Ann. 1996, 1951-1958. Griesbeck, A. G. Chimia 1998, 52, 272.
29. Hatanaka, Y.; Sato, Y.; Nakai, H.; Wada, M.; Mizoguchi, T.; Kanaoka, Y. Liebigs Ann. Chem. 1992, 1113. Sato, Y.; Nakai, H.; Wada, M.; Mizoguchi, T.; Hatanaka, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1992, 40, 3174. Takechi, H.; Tateuchi, S.; Machida, M.; Nishibata, Y.; Aoe, K.; Sato, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1986, 34, 3142. Sato, Y.; Nakai, H.; Wada, M.; Ogiwara, H.; Mizoguchi, T.; Migita, Y.; Hatanaka, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1982, 30, 1639.
30. Hatanaka, Y.; Sato, Y.; Nakai, H.; Wada, M.; Mizoguchi, T.; Kanaoka, Y. Liebigs Ann. Chem. 1992, 1113. Sato, Y.; Nakai, H.; Wada, M.; Mizoguchi, T.; Hatanaka, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1992, 40, 3174. Takechi, H.; Tateuchi, S.; Machida, M.; Nishibata, Y.; Aoe, K.; Sato, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1986, 34, 3142. Sato, Y.; Nakai, H.; Wada, M.; Ogiwara, H.; Mizoguchi, T.; Migita, Y.; Hatanaka, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1982, 30, 1639.
31. Hatanaka, Y.; Sato, Y.; Nakai, H.; Wada, M.; Mizoguchi, T.; Kanaoka, Y. Liebigs Ann. Chem. 1992, 1113. Sato, Y.; Nakai, H.; Wada, M.; Mizoguchi, T.; Hatanaka, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1992, 40, 3174. Takechi, H.; Tateuchi, S.; Machida, M.; Nishibata, Y.; Aoe, K.; Sato, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1986, 34, 3142. Sato, Y.; Nakai, H.; Wada, M.; Ogiwara, H.; Mizoguchi, T.; Migita, Y.; Hatanaka, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1982, 30, 1639.
32. Hatanaka, Y.; Sato, Y.; Nakai, H.; Wada, M.; Mizoguchi, T.; Kanaoka, Y. Liebigs Ann. Chem. 1992, 1113. Sato, Y.; Nakai, H.; Wada, M.; Mizoguchi, T.; Hatanaka, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1992, 40, 3174. Takechi, H.; Tateuchi, S.; Machida, M.; Nishibata, Y.; Aoe, K.; Sato, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1986, 34, 3142. Sato, Y.; Nakai, H.; Wada, M.; Ogiwara, H.; Mizoguchi, T.; Migita, Y.; Hatanaka, Y.; Kanaoka, Y. Chem. Pharm. Bull. 1982, 30, 1639.
33. Griesbeck, A. G.; Henz, A. Synlett 1994, 931.
34. Oelgemöller, M.; Griesbeck, A. G.; Kramer, W.; Nerowski, F. J. Inf. Rec. 1998, 24, 87-94, Griesbeck, A. G., Oelgemöller, M., Lex, J. Org. Letters, submitted. Oelgemöller, M. Dissertation, University of Cologne, 1999.
35. Oelgemöller, M.; Griesbeck, A. G.; Kramer, W.; Nerowski, F. J. Inf. Rec. 1998, 24, 87-94, Griesbeck, A. G., Oelgemöller, M., Lex, J. Org. Letters, submitted. Oelgemöller, M. Dissertation, University of Cologne, 1999.
36. Oelgemöller, M.; Griesbeck, A. G.; Kramer, W.; Nerowski, F. J. Inf. Rec. 1998, 24, 87-94, Griesbeck, A. G., Oelgemöller, M., Lex, J. Org. Letters, submitted. Oelgemöller, M. Dissertation, University of Cologne, 1999.
37. Griesbeck, A. G.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1995, 107, 498; Angew. Chem. Int. Ed. Engl. 1995, 34, 474.
38. Griesbeck, A. G.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1995, 107, 498; Angew. Chem. Int. Ed. Engl. 1995, 34, 474.
39. Griesbeck, A. G.; Henz, A.; Kramer, W.; Lex, J.; Nerowski, F.; Oelgemöller, M.; Peters, K.; Peters, E.-M. Helv. Chim. Acta 1997, 80, 912; Kramer, W.; Griesbeck, A. G.; Nerowski, F.; Oelgemöller, M. J. Inf. Rec. 1998, 24, 81.
40. Griesbeck, A. G.; Henz, A.; Kramer, W.; Lex, J.; Nerowski, F.; Oelgemöller, M.; Peters, K.; Peters, E.-M. Helv. Chim. Acta 1997, 80, 912; Kramer, W.; Griesbeck, A. G.; Nerowski, F.; Oelgemöller, M. J. Inf. Rec. 1998, 24, 81.
41. Hintz, S.; Heidbreder, A.; Mattay, J. Top. Curr. Chem. 1996, 177, 77.
42. Barton, D. H. R.; Crich, D.; Kretzschmar, G. J. Chem. Soc., Perkin Trans. I 1986, 39, Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901. Barton, D. H. R.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1987, 43, 4297. Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1987, 43, 4321.
43. Barton, D. H. R.; Crich, D.; Kretzschmar, G. J. Chem. Soc., Perkin Trans. I 1986, 39, Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901. Barton, D. H. R.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1987, 43, 4297. Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1987, 43, 4321.
44. Barton, D. H. R.; Crich, D.; Kretzschmar, G. J. Chem. Soc., Perkin Trans. I 1986, 39, Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901. Barton, D. H. R.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1987, 43, 4297. Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1987, 43, 4321.
45. Barton, D. H. R.; Crich, D.; Kretzschmar, G. J. Chem. Soc., Perkin Trans. I 1986, 39, Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901. Barton, D. H. R.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1987, 43, 4297. Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1987, 43, 4321.
46. Griesbeck, A. G., Oelgemöller, M. Synlett 1999, 492.
47. Griesbeck, A. G.; Mauder, H.; Müller, I. Chem. Ber. 1992, 125, 2467.
48. Griesbeck, A. G., Nerowski, F., Lex, J. J. Org. Chem. 1999, in print.
49. Yoon, U. C.; Oh, S. W.; Lee, C. W. Heterocycles 1995, 41, 2665.
50. Yoon, U. C.; Kim, D. U.; Lee, J. G.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698. Yoon, U. C.; Kim, D. U.; Kim, J. C.; Lee, C. W.; Choi, Y. S.; Mariano, P. S.; Lee, Y. J.; Ammon, H. L. Tetrahedron Lett. 1993, 34, 5859.
51. Yoon, U. C.; Kim, D. U.; Lee, J. G.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698. Yoon, U. C.; Kim, D. U.; Kim, J. C.; Lee, C. W.; Choi, Y. S.; Mariano, P. S.; Lee, Y. J.; Ammon, H. L. Tetrahedron Lett. 1993, 34, 5859.
52. Yoon, U. C.; Cho, S. J.; Lee, Y.-J.; Mancheno, M. J.; Mariano, P. S. J. Org. Chem. 1995, 60, 2353.
53. Griesbeck, A. G.; Dörr, H.; Nerowski, F. unpublished results.
54. Fuji, K.; Kawabata, T. Chem. Eur. J. 1998, 4, 373.
55. Griesbeck, A. G., Kramer, W., Lex, J. submitted to J. Am. Chem. Soc.