Studies on the enantioselective catalysis of photochemically promoted transformations: "Sensitizing receptors" as chiral catalysts

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 15-21

  Cauble, David F ^a   Lynch, Vincent ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL MOLECULAR RECEPTORS;

ENERGY TRANSFER; PHOTOCHEMICAL REACTIONS; SOLUTIONS; STOICHIOMETRY;

CATALYSIS;

ALKENE; QUINOLONE; RECEPTOR;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; ENERGY TRANSFER; PHOTOCHEMISTRY; REACTION ANALYSIS;

BENZOPHENONES; BINDING SITES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HETEROCYCLIC COMPOUNDS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; QUINOLONES; STEREOISOMERISM;

EID: 0037428013     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020630e     Document Type: Article

References (66)

1. For selected reviews on photochemistry in natural product synthesis, see: (a) Bach, T. Synthesis 1998, 683. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453. (d) Demuth, M. Pure Appl. Chem. 1986, 58, 1233.
2. For selected reviews on photochemistry in natural product synthesis, see: (a) Bach, T. Synthesis 1998, 683. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453. (d) Demuth, M. Pure Appl. Chem. 1986, 58, 1233.
3. For selected reviews on photochemistry in natural product synthesis, see: (a) Bach, T. Synthesis 1998, 683. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453. (d) Demuth, M. Pure Appl. Chem. 1986, 58, 1233.
4. For selected reviews on photochemistry in natural product synthesis, see: (a) Bach, T. Synthesis 1998, 683. (b) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003. (c) Crimmins, M. T. Chem. Rev. 1988, 88, 1453. (d) Demuth, M. Pure Appl. Chem. 1986, 58, 1233.
5. For selected reviews on enantioselective photochemistry and solution-state asymmetric photochemistry, see: (a) Inoue, Y. Chem. Rev. 1992, 92, 741. (b) Rao, H. Chem. Rev. 1983, 83, 535.
6. For selected reviews on enantioselective photochemistry and solution-state asymmetric photochemistry, see: (a) Inoue, Y. Chem. Rev. 1992, 92, 741. (b) Rao, H. Chem. Rev. 1983, 83, 535.
7. For selected examples of diastereoselective photochemical transformations, see: (a) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. J. Am. Chem. Soc. 1998, 120, 1747. (b) Alibes, R.; Bourdelande, J. L.; Font, J.; Gregori, A.; Parella, T. Tetrahedron 1996, 52, 1267. (c) Alibes, R.; Bourdelande, J. L.; Font, J.; Parella, T. Tetrahedron 1996, 52, 1279. (d) Carreira, E. M.; Hastings, C. A.; Shepard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc. 1994, 116, 6622. (e) Organ, M. G.; Froese, R. D.; Goddard, J. D.; Taylor, N. J.; Lange, G. L. J. Am. Chem. Soc. 1994, 116, 3312.
8. For selected examples of diastereoselective photochemical transformations, see: (a) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. J. Am. Chem. Soc. 1998, 120, 1747. (b) Alibes, R.; Bourdelande, J. L.; Font, J.; Gregori, A.; Parella, T. Tetrahedron 1996, 52, 1267. (c) Alibes, R.; Bourdelande, J. L.; Font, J.; Parella, T. Tetrahedron 1996, 52, 1279. (d) Carreira, E. M.; Hastings, C. A.; Shepard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc. 1994, 116, 6622. (e) Organ, M. G.; Froese, R. D.; Goddard, J. D.; Taylor, N. J.; Lange, G. L. J. Am. Chem. Soc. 1994, 116, 3312.
9. For selected examples of diastereoselective photochemical transformations, see: (a) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. J. Am. Chem. Soc. 1998, 120, 1747. (b) Alibes, R.; Bourdelande, J. L.; Font, J.; Gregori, A.; Parella, T. Tetrahedron 1996, 52, 1267. (c) Alibes, R.; Bourdelande, J. L.; Font, J.; Parella, T. Tetrahedron 1996, 52, 1279. (d) Carreira, E. M.; Hastings, C. A.; Shepard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc. 1994, 116, 6622. (e) Organ, M. G.; Froese, R. D.; Goddard, J. D.; Taylor, N. J.; Lange, G. L. J. Am. Chem. Soc. 1994, 116, 3312.
10. For selected examples of diastereoselective photochemical transformations, see: (a) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. J. Am. Chem. Soc. 1998, 120, 1747. (b) Alibes, R.; Bourdelande, J. L.; Font, J.; Gregori, A.; Parella, T. Tetrahedron 1996, 52, 1267. (c) Alibes, R.; Bourdelande, J. L.; Font, J.; Parella, T. Tetrahedron 1996, 52, 1279. (d) Carreira, E. M.; Hastings, C. A.; Shepard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc. 1994, 116, 6622. (e) Organ, M. G.; Froese, R. D.; Goddard, J. D.; Taylor, N. J.; Lange, G. L. J. Am. Chem. Soc. 1994, 116, 3312.
11. For selected examples of diastereoselective photochemical transformations, see: (a) Crimmins, M. T.; Wang, Z.; McKerlie, L. A. J. Am. Chem. Soc. 1998, 120, 1747. (b) Alibes, R.; Bourdelande, J. L.; Font, J.; Gregori, A.; Parella, T. Tetrahedron 1996, 52, 1267. (c) Alibes, R.; Bourdelande, J. L.; Font, J.; Parella, T. Tetrahedron 1996, 52, 1279. (d) Carreira, E. M.; Hastings, C. A.; Shepard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc. 1994, 116, 6622. (e) Organ, M. G.; Froese, R. D.; Goddard, J. D.; Taylor, N. J.; Lange, G. L. J. Am. Chem. Soc. 1994, 116, 3312.
12. For representative examples of chiral auxiliaries in photochemical transformations, see: (a) Dussault, P. H.; Han, Q.; Sloss, D. G.; Symonsbergen, D. J. Tetrahedron 1999, 55, 11437. (b) Bertrand, S.; Hoffman, N.; Pete, J.-P. Tetrahedron 1998, 54, 4873. (c) Yamaguchi, T.; Uchida, K.; Irie, M. J. Am. Chem. Soc. 1997, 119, 6066. (d) Faure, S.; Piva-Le Blanc, S.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1997, 38, 1045.
13. For representative examples of chiral auxiliaries in photochemical transformations, see: (a) Dussault, P. H.; Han, Q.; Sloss, D. G.; Symonsbergen, D. J. Tetrahedron 1999, 55, 11437. (b) Bertrand, S.; Hoffman, N.; Pete, J.-P. Tetrahedron 1998, 54, 4873. (c) Yamaguchi, T.; Uchida, K.; Irie, M. J. Am. Chem. Soc. 1997, 119, 6066. (d) Faure, S.; Piva-Le Blanc, S.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1997, 38, 1045.
14. For representative examples of chiral auxiliaries in photochemical transformations, see: (a) Dussault, P. H.; Han, Q.; Sloss, D. G.; Symonsbergen, D. J. Tetrahedron 1999, 55, 11437. (b) Bertrand, S.; Hoffman, N.; Pete, J.-P. Tetrahedron 1998, 54, 4873. (c) Yamaguchi, T.; Uchida, K.; Irie, M. J. Am. Chem. Soc. 1997, 119, 6066. (d) Faure, S.; Piva-Le Blanc, S.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1997, 38, 1045.
15. For representative examples of chiral auxiliaries in photochemical transformations, see: (a) Dussault, P. H.; Han, Q.; Sloss, D. G.; Symonsbergen, D. J. Tetrahedron 1999, 55, 11437. (b) Bertrand, S.; Hoffman, N.; Pete, J.-P. Tetrahedron 1998, 54, 4873. (c) Yamaguchi, T.; Uchida, K.; Irie, M. J. Am. Chem. Soc. 1997, 119, 6066. (d) Faure, S.; Piva-Le Blanc, S.; Piva, O.; Pete, J.-P. Tetrahedron Lett. 1997, 38, 1045.
16. For selected examples of enantioselective solid-state photochemistry, see: (a) Takahashi, M.; Sekine, N.; Fujita, T.; Watanabe, S.; Yamaguchi, K.; Sakamoto, M. J. Am. Chem. Soc. 1998, 120, 12770. (b) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1997, 119, 1462. (c) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. Pure Appl. Chem. 1997, 69, 815. (d) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203.
17. For selected examples of enantioselective solid-state photochemistry, see: (a) Takahashi, M.; Sekine, N.; Fujita, T.; Watanabe, S.; Yamaguchi, K.; Sakamoto, M. J. Am. Chem. Soc. 1998, 120, 12770. (b) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1997, 119, 1462. (c) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. Pure Appl. Chem. 1997, 69, 815. (d) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203.
18. For selected examples of enantioselective solid-state photochemistry, see: (a) Takahashi, M.; Sekine, N.; Fujita, T.; Watanabe, S.; Yamaguchi, K.; Sakamoto, M. J. Am. Chem. Soc. 1998, 120, 12770. (b) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1997, 119, 1462. (c) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. Pure Appl. Chem. 1997, 69, 815. (d) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203.
19. For selected examples of enantioselective solid-state photochemistry, see: (a) Takahashi, M.; Sekine, N.; Fujita, T.; Watanabe, S.; Yamaguchi, K.; Sakamoto, M. J. Am. Chem. Soc. 1998, 120, 12770. (b) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1997, 119, 1462. (c) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. Pure Appl. Chem. 1997, 69, 815. (d) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203.
20. For selected examples of enantioselective photochemistry in clathrates, see: (a) Toda, F.; Miyamoto, H.; Tamashima, T.; Kondo, M.; Ohashi, Y. J. Org. Chem. 1999, 64, 2690. (b) Toda, F. Acc. Chem. Res. 1995, 28, 480.
21. For selected examples of enantioselective photochemistry in clathrates, see: (a) Toda, F.; Miyamoto, H.; Tamashima, T.; Kondo, M.; Ohashi, Y. J. Org. Chem. 1999, 64, 2690. (b) Toda, F. Acc. Chem. Res. 1995, 28, 480.
22. For selected examples of enantioselective photochemistry in zeolites, see: (a) Sen, S. E.; Smith, S. M.; Sullivan, K. A. Tetrahedron 1999, 55, 12657. (b) Joy, A.; Scheffer, J. R.; Corbin, D. R.; Ramamurthy, V. J. Chem. Soc., Chem. Commun. 1998, 1379. (c) Joy, A.; Robbins, R. J.; Pitchumani, K.; Ramamurthy, V. Tetrahedron Lett. 1997, 38, 8825. (d) Kaprinidis, N. A.; Landis, M. S.; Turro, N. J. Tetrahedron Lett. 1997, 38, 2609.
23. For selected examples of enantioselective photochemistry in zeolites, see: (a) Sen, S. E.; Smith, S. M.; Sullivan, K. A. Tetrahedron 1999, 55, 12657. (b) Joy, A.; Scheffer, J. R.; Corbin, D. R.; Ramamurthy, V. J. Chem. Soc., Chem. Commun. 1998, 1379. (c) Joy, A.; Robbins, R. J.; Pitchumani, K.; Ramamurthy, V. Tetrahedron Lett. 1997, 38, 8825. (d) Kaprinidis, N. A.; Landis, M. S.; Turro, N. J. Tetrahedron Lett. 1997, 38, 2609.
24. For selected examples of enantioselective photochemistry in zeolites, see: (a) Sen, S. E.; Smith, S. M.; Sullivan, K. A. Tetrahedron 1999, 55, 12657. (b) Joy, A.; Scheffer, J. R.; Corbin, D. R.; Ramamurthy, V. J. Chem. Soc., Chem. Commun. 1998, 1379. (c) Joy, A.; Robbins, R. J.; Pitchumani, K.; Ramamurthy, V. Tetrahedron Lett. 1997, 38, 8825. (d) Kaprinidis, N. A.; Landis, M. S.; Turro, N. J. Tetrahedron Lett. 1997, 38, 2609.
25. For selected examples of enantioselective photochemistry in zeolites, see: (a) Sen, S. E.; Smith, S. M.; Sullivan, K. A. Tetrahedron 1999, 55, 12657. (b) Joy, A.; Scheffer, J. R.; Corbin, D. R.; Ramamurthy, V. J. Chem. Soc., Chem. Commun. 1998, 1379. (c) Joy, A.; Robbins, R. J.; Pitchumani, K.; Ramamurthy, V. Tetrahedron Lett. 1997, 38, 8825. (d) Kaprinidis, N. A.; Landis, M. S.; Turro, N. J. Tetrahedron Lett. 1997, 38, 2609.
26. Bach, T.; Bergmann, H.; Grosch, B.; Harms, K. J. Am. Chem. Soc. 2002, 124, 7982 and references therein.
27. For selected examples of photochemical reactions in chiral solvents, see: (a) Boyd, D. R.; Campbell, R. M.; Coulter, P. B.; Grimshaw, J.; Neill, D. C.; Jennings, W. B. J. Chem. Soc., Perkin Trans. 1 1985, 849. (b) Seebach, D.; Oei, H.-A.; Daum, H. Chem. Ber. 1977, 110, 2316. (c) Brittain, H. G.; Richardson, F. S. J. Phys. Chem. 1976, 80, 2590. (d) Seebach, D.; Oei, H. A. Angew. Chem., Int. Ed. Engl. 1975, 14, 629-636. (e) Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795.
28. For selected examples of photochemical reactions in chiral solvents, see: (a) Boyd, D. R.; Campbell, R. M.; Coulter, P. B.; Grimshaw, J.; Neill, D. C.; Jennings, W. B. J. Chem. Soc., Perkin Trans. 1 1985, 849. (b) Seebach, D.; Oei, H.-A.; Daum, H. Chem. Ber. 1977, 110, 2316. (c) Brittain, H. G.; Richardson, F. S. J. Phys. Chem. 1976, 80, 2590. (d) Seebach, D.; Oei, H. A. Angew. Chem., Int. Ed. Engl. 1975, 14, 629-636. (e) Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795.
29. For selected examples of photochemical reactions in chiral solvents, see: (a) Boyd, D. R.; Campbell, R. M.; Coulter, P. B.; Grimshaw, J.; Neill, D. C.; Jennings, W. B. J. Chem. Soc., Perkin Trans. 1 1985, 849. (b) Seebach, D.; Oei, H.-A.; Daum, H. Chem. Ber. 1977, 110, 2316. (c) Brittain, H. G.; Richardson, F. S. J. Phys. Chem. 1976, 80, 2590. (d) Seebach, D.; Oei, H. A. Angew. Chem., Int. Ed. Engl. 1975, 14, 629-636. (e) Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795.
30. For selected examples of photochemical reactions in chiral solvents, see: (a) Boyd, D. R.; Campbell, R. M.; Coulter, P. B.; Grimshaw, J.; Neill, D. C.; Jennings, W. B. J. Chem. Soc., Perkin Trans. 1 1985, 849. (b) Seebach, D.; Oei, H.-A.; Daum, H. Chem. Ber. 1977, 110, 2316. (c) Brittain, H. G.; Richardson, F. S. J. Phys. Chem. 1976, 80, 2590. (d) Seebach, D.; Oei, H. A. Angew. Chem., Int. Ed. Engl. 1975, 14, 629-636. (e) Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795.
31. For selected examples of photochemical reactions in chiral solvents, see: (a) Boyd, D. R.; Campbell, R. M.; Coulter, P. B.; Grimshaw, J.; Neill, D. C.; Jennings, W. B. J. Chem. Soc., Perkin Trans. 1 1985, 849. (b) Seebach, D.; Oei, H.-A.; Daum, H. Chem. Ber. 1977, 110, 2316. (c) Brittain, H. G.; Richardson, F. S. J. Phys. Chem. 1976, 80, 2590. (d) Seebach, D.; Oei, H. A. Angew. Chem., Int. Ed. Engl. 1975, 14, 629-636. (e) Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795.
32. For selected examples of photochemical reactions in chiral liquid crystals, see: (a) Finzi, L.; Maccagnani, G., Masiero, S.; Samari, R., Zani, P. Liq. Cryst. 1989, 6, 199. (b) Hilbert, M.; Solladie, G. J. Org. Chem. 1980, 45, 5393. (c) Eskanazi, C.; Nicoud, J. F.; Kagan, H. B. J. Org. Chem. 1979, 44, 995-999. (d) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1979, 1086. (e) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Chem. Lett. 1978, 863.
33. For selected examples of photochemical reactions in chiral liquid crystals, see: (a) Finzi, L.; Maccagnani, G., Masiero, S.; Samari, R., Zani, P. Liq. Cryst. 1989, 6, 199. (b) Hilbert, M.; Solladie, G. J. Org. Chem. 1980, 45, 5393. (c) Eskanazi, C.; Nicoud, J. F.; Kagan, H. B. J. Org. Chem. 1979, 44, 995-999. (d) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1979, 1086. (e) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Chem. Lett. 1978, 863.
34. For selected examples of photochemical reactions in chiral liquid crystals, see: (a) Finzi, L.; Maccagnani, G., Masiero, S.; Samari, R., Zani, P. Liq. Cryst. 1989, 6, 199. (b) Hilbert, M.; Solladie, G. J. Org. Chem. 1980, 45, 5393. (c) Eskanazi, C.; Nicoud, J. F.; Kagan, H. B. J. Org. Chem. 1979, 44, 995-999. (d) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1979, 1086. (e) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Chem. Lett. 1978, 863.
35. For selected examples of photochemical reactions in chiral liquid crystals, see: (a) Finzi, L.; Maccagnani, G., Masiero, S.; Samari, R., Zani, P. Liq. Cryst. 1989, 6, 199. (b) Hilbert, M.; Solladie, G. J. Org. Chem. 1980, 45, 5393. (c) Eskanazi, C.; Nicoud, J. F.; Kagan, H. B. J. Org. Chem. 1979, 44, 995-999. (d) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1979, 1086. (e) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Chem. Lett. 1978, 863.
36. For selected examples of photochemical reactions in chiral liquid crystals, see: (a) Finzi, L.; Maccagnani, G., Masiero, S.; Samari, R., Zani, P. Liq. Cryst. 1989, 6, 199. (b) Hilbert, M.; Solladie, G. J. Org. Chem. 1980, 45, 5393. (c) Eskanazi, C.; Nicoud, J. F.; Kagan, H. B. J. Org. Chem. 1979, 44, 995-999. (d) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Maeda, M. J. Chem. Soc., Chem. Commun. 1979, 1086. (e) Nakazaki, M.; Yamamoto, K.; Fujiwara, K.; Chem. Lett. 1978, 863.
37. For selected examples of photochemical reactions in chiral polymer matrixes, see: Tazuke, S.; Miyamoto, Y.; Ikeda, T.; Tachibana, K. Chem. Lett. 1986, 953.
38. For selected reviews on photochemistry in organized media, see: (a) Weiss, R. G. Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; Chapter 14. (b) Ganapathy, S.; Weiss, R. G. Organic Phototransformations in Nonhomogeneous Media; Fox, M. A., Ed., American Chemical Society: Washington, DC, 1985; Chapter 10.
39. For selected reviews on photochemistry in organized media, see: (a) Weiss, R. G. Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; Chapter 14. (b) Ganapathy, S.; Weiss, R. G. Organic Phototransformations in Nonhomogeneous Media; Fox, M. A., Ed., American Chemical Society: Washington, DC, 1985; Chapter 10.
40. Obata, T.; Tetsuro, S.; Yasutake, M.; Shinmyozu, T.; Kawaminami, M.; Yoshida, R.; Somekawa, K. Tetrahedron 2001, 57, 1531 and references therein.
41. For selected examples of enantioselective photochemistry via circularly polarized lasers, see: (a) Feringa, B. L.; van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3418. (b) Salam, A.; Meath, W. J. J. Chem. Phys. 1997, 106, 7865. (c) Salam, A.; Meath, W. J. Chem. Phys. Lett. 1997, 277, 199. (d) Shimizu, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1275. (e) Moradpour, A.; Kagan, H.; Baes, M.; Morren, G.; Martin, R. H. Tetrahedron 1975, 31, 2139.
42. For selected examples of enantioselective photochemistry via circularly polarized lasers, see: (a) Feringa, B. L.; van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3418. (b) Salam, A.; Meath, W. J. J. Chem. Phys. 1997, 106, 7865. (c) Salam, A.; Meath, W. J. Chem. Phys. Lett. 1997, 277, 199. (d) Shimizu, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1275. (e) Moradpour, A.; Kagan, H.; Baes, M.; Morren, G.; Martin, R. H. Tetrahedron 1975, 31, 2139.
43. For selected examples of enantioselective photochemistry via circularly polarized lasers, see: (a) Feringa, B. L.; van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3418. (b) Salam, A.; Meath, W. J. J. Chem. Phys. 1997, 106, 7865. (c) Salam, A.; Meath, W. J. Chem. Phys. Lett. 1997, 277, 199. (d) Shimizu, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1275. (e) Moradpour, A.; Kagan, H.; Baes, M.; Morren, G.; Martin, R. H. Tetrahedron 1975, 31, 2139.
44. For selected examples of enantioselective photochemistry via circularly polarized lasers, see: (a) Feringa, B. L.; van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3418. (b) Salam, A.; Meath, W. J. J. Chem. Phys. 1997, 106, 7865. (c) Salam, A.; Meath, W. J. Chem. Phys. Lett. 1997, 277, 199. (d) Shimizu, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1275. (e) Moradpour, A.; Kagan, H.; Baes, M.; Morren, G.; Martin, R. H. Tetrahedron 1975, 31, 2139.
45. For selected examples of enantioselective photochemistry via circularly polarized lasers, see: (a) Feringa, B. L.; van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3418. (b) Salam, A.; Meath, W. J. J. Chem. Phys. 1997, 106, 7865. (c) Salam, A.; Meath, W. J. Chem. Phys. Lett. 1997, 277, 199. (d) Shimizu, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1275. (e) Moradpour, A.; Kagan, H.; Baes, M.; Morren, G.; Martin, R. H. Tetrahedron 1975, 31, 2139.
46. For selected examples of enantioselective photochemistry via chiral photosensitizers, see: (a) Asaoka, S.; Kitazawa, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 8486. (b) Inoue, Y.; Matsushima, E.; Takehiko, W. J. Am. Chem. Soc. 1998, 120, 10687. (c) Inoue, Y.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1997, 119, 472. (d) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1993, 58, 1011. (e) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332. (f) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
47. For selected examples of enantioselective photochemistry via chiral photosensitizers, see: (a) Asaoka, S.; Kitazawa, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 8486. (b) Inoue, Y.; Matsushima, E.; Takehiko, W. J. Am. Chem. Soc. 1998, 120, 10687. (c) Inoue, Y.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1997, 119, 472. (d) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1993, 58, 1011. (e) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332. (f) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
48. For selected examples of enantioselective photochemistry via chiral photosensitizers, see: (a) Asaoka, S.; Kitazawa, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 8486. (b) Inoue, Y.; Matsushima, E.; Takehiko, W. J. Am. Chem. Soc. 1998, 120, 10687. (c) Inoue, Y.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1997, 119, 472. (d) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1993, 58, 1011. (e) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332. (f) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
49. For selected examples of enantioselective photochemistry via chiral photosensitizers, see: (a) Asaoka, S.; Kitazawa, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 8486. (b) Inoue, Y.; Matsushima, E.; Takehiko, W. J. Am. Chem. Soc. 1998, 120, 10687. (c) Inoue, Y.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1997, 119, 472. (d) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1993, 58, 1011. (e) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332. (f) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
50. For selected examples of enantioselective photochemistry via chiral photosensitizers, see: (a) Asaoka, S.; Kitazawa, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 8486. (b) Inoue, Y.; Matsushima, E.; Takehiko, W. J. Am. Chem. Soc. 1998, 120, 10687. (c) Inoue, Y.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1997, 119, 472. (d) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1993, 58, 1011. (e) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332. (f) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
51. For selected examples of enantioselective photochemistry via chiral photosensitizers, see: (a) Asaoka, S.; Kitazawa, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 1999, 121, 8486. (b) Inoue, Y.; Matsushima, E.; Takehiko, W. J. Am. Chem. Soc. 1998, 120, 10687. (c) Inoue, Y.; Tsuneishi, H.; Hakushi, T.; Tai, A. J. Am. Chem. Soc. 1997, 119, 472. (d) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1993, 58, 1011. (e) Inoue, Y.; Yamasaki, N.; Yokoyama, T.; Tai, A. J. Org. Chem. 1992, 57, 1332. (f) Inoue, Y.; Yokoyama, T.; Yamasaki, N.; Tai, A. J. Am. Chem. Soc. 1989, 111, 6480.
52. For asymmetric photodeconjugation, see: (a) Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.: Pete, J.-P. J. Am. Chem. Soc. 1990, 112, 9263. (b) Piva, O.; Pete, J.-P. Tetrahedron Lett. 1990, 31, 5157. (c) Pete, J.-P.; Heinin, F.; Mortezaei, R.; Muzart, J.; Piva, O. Pure Appl. Chem. 1986, 58, 1257.
53. For asymmetric photodeconjugation, see: (a) Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.: Pete, J.-P. J. Am. Chem. Soc. 1990, 112, 9263. (b) Piva, O.; Pete, J.-P. Tetrahedron Lett. 1990, 31, 5157. (c) Pete, J.-P.; Heinin, F.; Mortezaei, R.; Muzart, J.; Piva, O. Pure Appl. Chem. 1986, 58, 1257.
54. For asymmetric photodeconjugation, see: (a) Piva, O.; Mortezaei, R.; Henin, F.; Muzart, J.: Pete, J.-P. J. Am. Chem. Soc. 1990, 112, 9263. (b) Piva, O.; Pete, J.-P. Tetrahedron Lett. 1990, 31, 5157. (c) Pete, J.-P.; Heinin, F.; Mortezaei, R.; Muzart, J.; Piva, O. Pure Appl. Chem. 1986, 58, 1257.
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