Spin-selectivity in photochemistry: A tool for organic synthesis

Synlett

Volumn , Issue 4, 2003, Pages 451-472

  Griesbeck, Axel G ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

90 Rule; Biradicals; Photochemistry; Photocyclization; Photocycloaddition; Spin orbit coupling geometries

Indexed keywords

CARBONYL DERIVATIVE; OXETANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONCENTRATION RESPONSE; CYCLIZATION; MOLECULAR INTERACTION; PHOTOCHEMISTRY; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0037239957     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37505     Document Type: Article

References (146)

1. (a) Buchachenko, A. L. Chem. Rev. 1995, 95, 2507.
2. (b) Steiner, U.; Ulrich, T. Chem. Rev. 1989, 89, 51.
3. (c) For a definition of the term and a series of papers on this topic see: Mol. Physics 2002, 100 issues 8 and 9.
4. (d) Spincrossing effects in organometallic chemistry (two-state reactivity concept): Schröder, D.; Shaik, S.; Schwarz, H. Acc. Chem. Res. 2000, 33, 139.
5. Buchachenko, A. L. Pure Appl. Chem. 2000, 72, 2243.
6. (a) Porco, J. A.; Schreiber, S. L. In Comprehensive Organic Synthesis, 5; Trost, B., Ed.; Pergamon Press: New York, 1991, 151.
7. (b) Mattay, J.; Conrads, R.; Hoffmann, R. In Methoden der Organischen Chemie, Houben-Weyl, E21c; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: Stuttgart, 1995, 3133.
8. (c) Bach, T. Synthesis 1998, 683.
9. (d) Carless, H. A. J. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984, 425.
10. (e) Griesbeck, A. G. In Handbook of Organic Photochemistry and Photobiology; Horspool, W. M.; Song, P.-S., Eds.; CRC Press: Boca Raton, 1995, 550.
11. (f) Griesbeck, A. G. In Handbook of Organic Photochemistry and Photobiology; Horspool, W. M.; Song, P.-S., Eds.; CRC Press: Boca Raton, 1995, 755.
12. (a) Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3.
13. (b) Baldwin, S. W. In Organic Photochemistry, 5; Padwa, A., Ed.; Marcel Dekker: New York, 1981, 123.
14. (c) Demuth, M.; Gamal, M. Synthesis 1989, 145.
15. (d) Schuster, D. I. In The Chemistry of Enones, Vol. 2; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1989, 623.
16. (e) Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
17. (f) De Keukeleire, D.; He, S.-L. Chem. Rev. 1993, 93, 359.
18. (a) Wagner, P. J.; Park, B.-S. Organic Photochemistry, 11; Padwa, A., Ed.; Dekker: New York, Basel, 1991, 227.
19. (b) Wagner, P. J. In Handbook of Photochemistry and Photobiology; Horspool, W. M.; Song, P.-S., Eds.; CRC Press: Boca Raton, 1995, 449.
20. (c) Wagner, P. J. In Molecular Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Wiley-Interscience: New York, 1980, Chap. 20.
21. (a) Weuthen, M.; Scharf, H.-D.; Runsink, J.; Vaßen, R. Chem. Ber. 1988, 121, 971.
22. (b) Pelzer, R.; Jütten, P.; Scharf, H.-D. Chem. Ber. 1989, 122, 487.
23. Griesbeck, A. G.; Stadtmüller, S. J. Am. Chem. Soc. 1990, 112, 1281.
24. Griesbeck, A. G.; Mauder, H.; Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70.
25. Buhr, S.; Griesbeck, A. G.; Lex, J.; Mattay, J.; Schröer, J. Tetrahedron Lett. 1996, 37, 1195.
26. Hu, S.; Neckers, D. C. J. Org. Chem. 1997, 62, 564.
27. (a) Turro, N. J. Modern Molecular Photochemistry; Benjamin/Cummings Publishing Co.: Menlo Park: California, 1978, 434.
28. (b) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific Publications: London, 1991, 340.
29. Johnston, L. J.; Scaiano, J. C. Chem. Rev. 1989, 89, 521.
30. Salem, L.; Rowland, C. Angew. Chem., Int. Ed. Engl. 1972, 11, 92.
31. (a) Carlacci, L.; Doubleday, C. Jr.; Furlani, T. R.; King, H. F.; McIver, J. W. J. Am. Chem. Soc. 1987, 109, 5323.
32. (b) Doubleday, C. Jr.; Turro, N. J.; Wang, J.-F. Acc. Chem. Res. 1989, 22, 199.
33. (a) Michl, J. J. Am. Chem. Soc. 1996, 118, 3568.
34. (b) Michl, J.; Havlas, Z. Pure Appl. Chem. 1997, 69, 785.
35. (c) Havlas, Z.; Downing, J. W.; Michl, J. J. Phys. Chem., A 1998, 102, 5681.
36. Kita, F.; Nau, W. M.; Adam, W.; Wirz, J. J. Am. Chem. Soc. 1995, 117, 8670.
37. Turro, N. J. Modern Molecular Photochemistry; Benjamin/Cummings Publishing Co.: Menlo Park: California, 1978, 434.
38. (a) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1981, 103, 6255.
39. (b) Freilich, S. C.; Peters, K. S. J. Am. Chem. Soc. 1985, 107, 3819.
40. Klessinger, M. Pure Appl. Chem. 1997, 69, 773.
41. Reynolds, J. H.; Berson, J. A.; Kumashiro, K. K.; Duchamp, J. C.; Zilm, K. W.; Scaiano, J. C.; Berinstain, A. B.; Rubello, A.; Vogel, P. J. Am. Chem. Soc. 1993, 115, 8073.
42. Griesbeck, A. G.; Mauder, H.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Chem. Ber. 1991, 124, 407.
43. Griesbeck, A. G.; Stadtmüller, S. J. Am. Chem. Soc. 1991, 113, 6923.
44. Park, S.-K.; Lee, S.-J.; Baek, K.; Yu, C.-M. Bull. Korean Chem. Soc. 1998, 19, 35.
45. Abe, M.; Shirodai, Y.; Nojima, M. J. Chem. Soc., Perkin Trans. 1 1998, 3253.
46. (a) Sun, D. L.; Hubig, S. M.; Kochi, J. K. J. Org. Chem. 1999, 64, 2250.
47. (b) Hubig, S. M.; Sun, D. L.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 1999, 781.
48. (c) Bosch, E.; Hubig, S. M.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 386.
49. (a) Weller, A. Z. Phys. Chem. N. F. 1982, 130, 129.
50. (b) Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259.
51. Griesbeck, A. G.; Buhr, S.; Fiege, M.; Schmickler, H.; Lex, J. J. Org. Chem. 1998, 63, 3847.
52. (a) Eckert, G.; Goez, M. J. Am. Chem. Soc. 1994, 116, 11999.
53. (b) Goez, M.; Eckert, G. J. Am. Chem. Soc. 1996, 118, 140.
54. Abe, M.; Masayuki, I.; Nojima, M. J. Chem. Soc., Perkin Trans. 1 1998, 3261.
55. Thopate, S. R.; Kulkarni, M. G.; Puranik, V. G. Angew. Chem. Int. Ed 1998, 37, 1110.
56. Bach, T. Liebigs Ann. 1997, 1627.
57. (a) Bach, T. Tetrahedron Lett. 1991, 32, 7037.
58. (b) Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457.
59. Bach, T. Liebigs Ann. 1995, 855.
60. (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 884.
61. (b) Bach, T.; Schröder, J.; Brandl, T.; Hecht, J.; Harms, K. Tetrahedron 1998, 54, 4507.
62. Bach, T.; Brummerhop, H. Angew. Chem. Int. Ed. 1998, 37, 3400.
63. Bach, T.; Schröder, J. J. Org. Chem. 1999, 64, 1265.
64. Döpp, D.; Fischer, M.-A. Recl. Trav. Chim. Pays-Bas 1995, 114, 498.
65. (a) Ogata, M.; Watanabe, H.; Kano, H. Tetrahedron Lett. 1967, 533.
66. (b) Toki, S.; Sakurai, H. Tetrahedron Lett. 1967, 4119.
67. (c) Zamojski, A.; Kozluk, T. J. Org. Chem. 1977, 42, 1089.
68. (d) Evanega, G. R.; Whipple, E. B. Tetrahedron Lett. 1967, 2163
69. (e) Heatchcock, C. H.; Pirrung, M. C.; Montgomery, S. H.; Lampe, J. Tetrahedron 1981, 37, 4087.
70. (f) Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1983, 105, 6723.
71. (g) Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1984, 106, 4186.
72. (h) Schreiber, S. L.; Hoveyda, A. H.; Wu, H.-J. J. Am. Chem. Soc. 1984, 106, 1148.
73. (i) Schreiber, S. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1984, 106, 7200.
74. (a) Carless, H. A. J.; Halfhide, A. F. E. J. Chem. Soc., Perkin Trans. 1 1992, 1081.
75. (b) Schreiber, S. L.; Desmaele, D.; Porco, J. A. Jr. Tetrahedron Lett. 1988, 29, 6689.
76. (c) Schreiber, S. L.; Porco, J. A. Jr. J. Org. Chem. 1989, 54, 4721.
77. (d) Sekretár, S.; Rudá, J.; Stibrányi, L. Collect. Czech. Chem. Commun. 1984, 49, 71.
78. Rivas, C.; Pacheco, D.; Vargas, F.; Ascanio, J. J. Heterocycl. Chem. 1981, 18, 1065.
79. (a) Rivas, C.; Bolivar, R. A. J. Heteracycl. Chem. 1976, 13, 1037.
80. (b) Jones, G. I. I.; Gilow, H. M.; Low, J. J. Org. Chem. 1979, 44, 2949.
81. Matsuura, T.; Banba, A.; Ogura, K. Tetrahedron 1971, 27, 1211.
82. Nakano, T.; Rodriquez, W.; de Roche, S. Z.; Larrauri, J. M.; Rivas, C.; Pérez, P. J. Heteracycl. Chem. 1980, 17, 1777.
83. Hoye, T. R.; Richardson, W. S. J. Org. Chem. 1989, 54, 688.
84. Shima, K.; Kubota, T.; Sakurai, H. Bull. Chem. Soc. Jpn. 1976, 44, 2567.
85. Cantrell, T. S.; Allen, A. C.; Ziffer, H. J. Org. Chem. 1989, 54, 140.
86. Schreiber, S. L. Science 1989, 111, 5367.
87. Griesbeck, A. G.; Fiege, M.; Lex, J. Chem. Commun. 2000, 589.
88. Griesbeck, A. G.; Bondock, S. Can. J. Chem. 2003, in press.
89. Kutateladze, A. G. J. Am. Chem. Soc. 2001, 123, 9279.
90. Griesbeck, A. G.; Fiege, M.; Bondock, S.; Gudipati, M. S. Org. Lett. 2000, 2, 3623.
91. Palmer, I. J.; Ragazos, I. N.; Bernardi, F.; Olivucci, M.; Robb, M. A. J. Am. Chem. Soc. 1994, 116, 2121.
92. Griesbeck, A. G.; Bondock, S.; Gudipati, M. S. Angew. Chem. Int. Ed. 2001, 40, 4684.
93. Caldwell, R. A.; Hrncir, D. C.; Munoz, T. Jr.; Unett, D. J. J. Am. Chem. Soc. 1996, 118, 8741.
94. (a) Rudolph, A.; Weedon, A. C. Can. J. Chem. 1990, 68, 1590.
95. (b) Kaprinidis, N. A.; Lem, G.; Courtney, S. H.; Schuster, D. I. J. Am. Chem. Soc. 1993, 115, 3324.
96. Maradyn, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359.
97. (a) Corey, E. J.; Bass, J. D.; LeMahieu, R.; Mitra, R. B. J. Am. Chem. Soc. 1964, 84, 5570.
98. (b) Loutfy, R. O.; de Mayo, P. J. Am. Chem. Soc. 1977, 99, 3559.
99. (a) Hill, E. A.; Theissen, R. J.; Cannon, C. E.; Miller, R.; Guthrie, R. B.; Chen, A. T. J. Org. Chem. 1976, 41, 1191.
100. (b) Termont, D.; De Keukeleire, D.; Vandewalle, M. J. Chem. Soc., Perkin Trans. 1 1977, 2349.
101. Griesbeck, A. G.; Stadtmüller, S.; Bringmann, G.; Busse, H.; Buddrus, J. Chem. Ber. 1992, 125, 933.
102. (a) Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1991, 113, 8525.
103. (b) Andrew, D.; Hastings, D. J.; Oldroyd, D. L.; Rudolph, A.; Weedon, A. C.; Wong, D. F.; Zhang, B. Pure Appl. Chem. 1992, 64, 1327.
104. Yang, N. C.; Yang, D.-H. J. Am. Chem. Soc. 1958, 80, 2913.
105. (a) Dorigo, A. E.; McCarrick, M. A.; Loncharich, R. J.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 7508.
106. (b) Sauers, R. R.; Edberg, L. A. J. Org. Chem. 1994, 59, 7061.
107. (a) Ihmels, H.; Scheffer, J. R. Tetrahedron 1999, 55, 885.
108. (b) Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991, 185.
109. (c) Scheffer, J. R.; Garcia-Garibay, M.; Nalmasu, O. Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1987, 8.
110. (d) Scheffer, J. R. In Organic Solid State Chemistry; Desiraju, G. R., Ed.; Elsevier: Amsterdam, 1987, 1.
111. Wagner, P. J. In Handbook of Photochemistry and Photobiology; Horspool, W. M.; Song, P.-S., Eds.; CRC Press: Boca Raton, 1995, 459.
112. (a) Griesbeck, A. G. Chimia 1998, 63, 3847.
113. (b) Griesbeck, A. G. EPA Newletters 1998, 27, 70.
114. (c) Griesbeck, A. G. Liebigs Ann. Chem. 1996, 1951.
115. (a) Griesbeck, A. G.; Heckroth, H.; Lex, J. Chem. Commun. 1999, 1109.
116. (b) Griesbeck, A. G.; Heckroth, H. J. Am. Chem. Soc. 2002, 124, 396.
117. Yoshida, K.; Fueno, T. Bull. Soc. Chim. Jpn. 1987, 55, 229.
118. Leroy, C.; Peeters, D.; Wilante, C. Theochem. 1982, 5, 217.
119. (a) Scaiano, J. C. Tetrahedron 1982, 38, 819.
120. (b) Wagner, P. J.; Zand, A.; Park, B.-S. J. Am. Chem. Soc. 1996, 118, 12856.
121. Griesbeck, A. G.; Heckroth, H.; Schmickler, H. Tetrahedron Lett. 1999, 40, 3137.
122. Lindemann, U.; Reck, G.; Wulff-Molder, D.; Wessig, P. Tetrahedron 1998, 54, 2529.
123. (a) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843.
124. (b) Wessig, P.; Wettstein, P.; Giese, B.; Neuburger, M.; Zehnder, M. Helv. Chim. Acta 1994, 77, 829.
125. (c) Wyss, C.; Batra, R.; Lehmann, C.; Sauer, S.; Giese, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2529.
126. (a) Griesbeck, A. G.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 474.
127. (b) Griesbeck, A. G.; Henz, A.; Kramer, W.; Lex, J.; Nerowski, F.; Oelgemöller, M.; Peters, K.; Peters, E.-M. Helv. Chim. Acta 1997, 80, 912.
128. Griesbeck, A. G.; Nerowski, F.; Lex, J. J. Org. Chem. 1999, 64, 5213.
129. Griesbeck, A. G.; Kramer, W.; Oelgemöller, M. Synlett 1999, 1169.
130. (a) Görner, H.; Griesbeck, A. G.; Heinrich, T.; Kramer, W.; Oelgemöller, M. Chem.-Eur. J. 2001, 7, 1530.
131. (b) Görner, H.; Oelgemöller, M.; Griesbeck, A. G. J. Phys. Chem., A. 2002, 106, 1458.
132. Griesbeck, A. G.; Kramer, W.; Oelgemöller, M. Green Chem. 1999, 205.
133. Griesbeck, A. G.; Kramer, W.; Lex, J. Synthesis 2001, 1159.
134. Griesbeck, A. G.; Kramer, W.; Bartoschek, A.; Schmickler, S. Org. Lett. 2001, 3, 537.
135. Griesbeck, A. G.; Henz, A. Synlett 1994, 931.
136. (a) Yoon, U. C.; Kim, D. U.; Lee, J. G.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698.
137. (b) 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.
138. (a) Thurston, D. E.; Bose, D. S. Chem. Rev. 1994, 94, 433.
139. (b) Bose, D. S.; Thompson, A. S.; Ching, J.; Hartley, J.; Berardini, M. D.; Jenkins, T. C.; Neidle, S.; Hurley, L. H.; Thurston, D. E. J. Am. Chem. Soc. 1992, 114, 939.
140. (c) Thurston, D. E.; Morris, S. J.; Hartley, J. J. Chem. Soc., Chem. Commun. 1996, 563.
141. Griesbeck, A. G.; Kramer, W.; Lex, J. Angew. Chem. Int. Ed. 2001, 40, 577.
142. Fuji, K.; Kawabata, T. Chem.-Eur. J. 1998, 4, 373.
143. For other examples of this principle see: (a) Schmalz, H.-G.; de Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem. Int. Ed. 1999, 38, 1620. (b) Matsumura, Y.; Shirakawa, Y.; Satoh, Y.; Umino, M.; Tanaka, T.; Maki, T.; Onomura, O. Org. Lett. 2000, 2, 1689. (c) Sauer, S.; Schumacher, A.; Barbosa, F.; Giese, B. Tetrahedron Lett. 1998, 39, 3685. (d) Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem. Int. Ed. 1999, 38, 2586.
144. For other examples of this principle see: (a) Schmalz, H.-G.; de Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem. Int. Ed. 1999, 38, 1620. (b) Matsumura, Y.; Shirakawa, Y.; Satoh, Y.; Umino, M.; Tanaka, T.; Maki, T.; Onomura, O. Org. Lett. 2000, 2, 1689. (c) Sauer, S.; Schumacher, A.; Barbosa, F.; Giese, B. Tetrahedron Lett. 1998, 39, 3685. (d) Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem. Int. Ed. 1999, 38, 2586.
145. For other examples of this principle see: (a) Schmalz, H.-G.; de Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem. Int. Ed. 1999, 38, 1620. (b) Matsumura, Y.; Shirakawa, Y.; Satoh, Y.; Umino, M.; Tanaka, T.; Maki, T.; Onomura, O. Org. Lett. 2000, 2, 1689. (c) Sauer, S.; Schumacher, A.; Barbosa, F.; Giese, B. Tetrahedron Lett. 1998, 39, 3685. (d) Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem. Int. Ed. 1999, 38, 2586.
146. For other examples of this principle see: (a) Schmalz, H.-G.; de Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem. Int. Ed. 1999, 38, 1620. (b) Matsumura, Y.; Shirakawa, Y.; Satoh, Y.; Umino, M.; Tanaka, T.; Maki, T.; Onomura, O. Org. Lett. 2000, 2, 1689. (c) Sauer, S.; Schumacher, A.; Barbosa, F.; Giese, B. Tetrahedron Lett. 1998, 39, 3685. (d) Giese, B.; Wettstein, P.; Stähelin, C.; Barbosa, F.; Neuburger, M.; Zehnder, M.; Wessig, P. Angew. Chem. Int. Ed. 1999, 38, 2586.