Indium-Mediated Tandem Radical Addition-Cyclization-Trap Reactions in Aqueous Media

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3835-3838

  Ueda, Masafumi ^a   Miyabe, Hideto ^b   Nishimura, Azusa ^a   Miyata, Okiko ^a   Takemoto, Yoshiji ^b   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDRAZONE DERIVATIVE; INDIUM; RADICAL; SULFONAMIDE; UNCLASSIFIED DRUG; VINYL SULFONAMIDE;

ADDITION REACTION; ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CYCLIZATION; ELECTRON TRANSPORT; HYPOTHESIS; RADICAL REACTION;

EID: 0242712819     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035357x     Document Type: Article

References (54)

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11. For some examples, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 941. (b) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (c) Feldman, K. S.; Vong, A. K. K. Tetrahedron Lett. 1990, 31, 823. (d) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709. (e) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. (f) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011. (g) Takasu, K.; Ohsato, H.; Kuroyanagi, J.; Ihara, M. J. Org. Chem. 2002, 67, 6001. (h) Sibi, M. P.; Miyabe, H. Org. Lett. 2002, 4, 3435. (i) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
12. For some examples, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 941. (b) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (c) Feldman, K. S.; Vong, A. K. K. Tetrahedron Lett. 1990, 31, 823. (d) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709. (e) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. (f) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011. (g) Takasu, K.; Ohsato, H.; Kuroyanagi, J.; Ihara, M. J. Org. Chem. 2002, 67, 6001. (h) Sibi, M. P.; Miyabe, H. Org. Lett. 2002, 4, 3435. (i) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
13. For some examples, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 941. (b) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (c) Feldman, K. S.; Vong, A. K. K. Tetrahedron Lett. 1990, 31, 823. (d) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709. (e) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. (f) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011. (g) Takasu, K.; Ohsato, H.; Kuroyanagi, J.; Ihara, M. J. Org. Chem. 2002, 67, 6001. (h) Sibi, M. P.; Miyabe, H. Org. Lett. 2002, 4, 3435. (i) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
14. For some examples, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 941. (b) Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (c) Feldman, K. S.; Vong, A. K. K. Tetrahedron Lett. 1990, 31, 823. (d) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709. (e) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. (f) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011. (g) Takasu, K.; Ohsato, H.; Kuroyanagi, J.; Ihara, M. J. Org. Chem. 2002, 67, 6001. (h) Sibi, M. P.; Miyabe, H. Org. Lett. 2002, 4, 3435. (i) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
15. For some examples, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 941. (b) Curran, D. P.; Chen, M-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (c) Feldman, K. S.; Vong, A. K. K. Tetrahedron Lett. 1990, 31, 823. (d) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709. (e) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. (f) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011. (g) Takasu, K.; Ohsato, H.; Kuroyanagi, J.; Ihara, M. J. Org. Chem. 2002, 67, 6001. (h) Sibi, M. P.; Miyabe, H. Org. Lett 2002, 4, 3435. (i) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
16. For some examples, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 941. (b) Curran, D. P.; Chen, M-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (c) Feldman, K. S.; Vong, A. K. K. Tetrahedron Lett. 1990, 31, 823. (d) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709. (e) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. (f) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011. (g) Takasu, K.; Ohsato, H.; Kuroyanagi, J.; Ihara, M. J. Org. Chem. 2002, 67, 6001. (h) Sibi, M. P.; Miyabe, H. Org. Lett 2002, 4, 3435. (i) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
17. For some examples, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 941. (b) Curran, D. P.; Chen, M-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (c) Feldman, K. S.; Vong, A. K. K. Tetrahedron Lett. 1990, 31, 823. (d) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709. (e) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. (f) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011. (g) Takasu, K.; Ohsato, H.; Kuroyanagi, J.; Ihara, M. J. Org. Chem. 2002, 67, 6001. (h) Sibi, M. P.; Miyabe, H. Org. Lett 2002, 4, 3435. (i) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
18. For some examples, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 941. (b) Curran, D. P.; Chen, M-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872. (c) Feldman, K. S.; Vong, A. K. K. Tetrahedron Lett. 1990, 31, 823. (d) Tsuritani, T.; Shinokubo, H.; Oshima, K. Org. Lett. 2001, 3, 2709. (e) Sibi, M. P.; Chen, J.; Rheault, T. R. Org. Lett. 2001, 3, 3679. (f) Kitagawa, O.; Yamada, Y.; Sugawara, A.; Taguchi, T. Org. Lett. 2002, 4, 1011. (g) Takasu, K.; Ohsato, H.; Kuroyanagi, J.; Ihara, M. J. Org. Chem. 2002, 67, 6001. (h) Sibi, M. P.; Miyabe, H. Org. Lett 2002, 4, 3435. (i) Demircan, A.; Parsons, P. J. Eur. J. Org. Chem. 2003, 1729.
19. We have studied the tandem radical addition-cyclization reactions of oxime ether and hydrazone by using triethylborane as a radical initiator. Some of these reactions proceeded even in aqueous media. See: (a) Miyabe, H.; Ueda, M.; Fujii, K.; Nishimura, A.; Naito, T. J. Org. Chem. 2003, 68, 5618. (b) Miyabe, H.; Fujii, K.; Goto. T.; Naito, T. Org. Lett. 2000, 2, 4071. (c) Miyabe, H.; Fujii, K.; Tanaka, H.; Naito, T. Chem. Commun. 2001, 831.
20. We have studied the tandem radical addition-cyclization reactions of oxime ether and hydrazone by using triethylborane as a radical initiator. Some of these reactions proceeded even in aqueous media. See: (a) Miyabe, H.; Ueda, M.; Fujii, K.; Nishimura, A.; Naito, T. J. Org. Chem. 2003, 68, 5618. (b) Miyabe, H.; Fujii, K.; Goto. T.; Naito, T. Org. Lett. 2000, 2, 4071. (c) Miyabe, H.; Fujii, K.; Tanaka, H.; Naito, T. Chem. Commun. 2001, 831.
21. We have studied the tandem radical addition-cyclization reactions of oxime ether and hydrazone by using triethylborane as a radical initiator. Some of these reactions proceeded even in aqueous media. See: (a) Miyabe, H.; Ueda, M.; Fujii, K.; Nishimura, A.; Naito, T. J. Org. Chem. 2003, 68, 5618. (b) Miyabe, H.; Fujii, K.; Goto. T.; Naito, T. Org. Lett. 2000, 2, 4071. (c) Miyabe, H.; Fujii, K.; Tanaka, H.; Naito, T. Chem. Commun. 2001, 831.
22. Garner, P. P.; Parker, D. T.; Gajewski, J. J.; Lubineau, A.; Ange, J.; Queneau, Y.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Piermatti, O. ; Pizzo, F.; Kobayashi, S. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, UK, 1998.
23. For a recent review, see: (a) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (b) Podlech, J.; Maier, T. C. Synthesis 2003, 633.
24. For a recent review, see: (a) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (b) Podlech, J.; Maier, T. C. Synthesis 2003, 633.
25. For selected examples of aqueous-medium radical reactions, see: (a) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604. (b) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1998, 1351. (c) Kita, Y.; Nambu, H.; Ramesh, N. G.; Anikumar, G.; Matsugi, M. Org. Lett. 2001, 3, 1157. (d) Nambu, H.; Hata, K.; Matsugi, M.; Kita, Y. Chem. Commun. 2002, 1082.
26. For selected examples of aqueous-medium radical reactions, see: (a) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604. (b) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1998, 1351. (c) Kita, Y.; Nambu, H.; Ramesh, N. G.; Anikumar, G.; Matsugi, M. Org. Lett. 2001, 3, 1157. (d) Nambu, H.; Hata, K.; Matsugi, M.; Kita, Y. Chem. Commun. 2002, 1082.
27. For selected examples of aqueous-medium radical reactions, see: (a) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604. (b) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1998, 1351. (c) Kita, Y.; Nambu, H.; Ramesh, N. G.; Anikumar, G.; Matsugi, M. Org. Lett. 2001, 3, 1157. (d) Nambu, H.; Hata, K.; Matsugi, M.; Kita, Y. Chem. Commun. 2002, 1082.
28. For selected examples of aqueous-medium radical reactions, see: (a) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604. (b) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1998, 1351. (c) Kita, Y.; Nambu, H.; Ramesh, N. G.; Anikumar, G.; Matsugi, M. Org. Lett. 2001, 3, 1157. (d) Nambu, H.; Hata, K.; Matsugi, M.; Kita, Y. Chem. Commun. 2002, 1082.
29. For our indium-mediated radical reactions, see: (a) Miyabe, H.; Ueda, M. ; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131. (b) Miyabe, H.; Nishimura, A.; Ueda, M.; Naito, T. Chem. Commun. 2002, 1454.
30. For our indium-mediated radical reactions, see: (a) Miyabe, H.; Ueda, M. ; Nishimura, A.; Naito, T. Org. Lett. 2002, 4, 131. (b) Miyabe, H.; Nishimura, A.; Ueda, M.; Naito, T. Chem. Commun. 2002, 1454.
31. Recently, three related indium-mediated radical reactions were reported. See: (a) Huang, T.; Keh, C. C. K.; Li, C.-J. Chem. Commun. 2002, 2440. (b) Yanada, R.; Nishimori, N.; Matsumura, A.; Fujii, N.; Takemoto, Y. Tetrahedron Lett. 2002, 43, 4585. (c) Jang, D. O.; Cho, D. H. Synlett 2002, 631.
32. Recently, three related indium-mediated radical reactions were reported. See: (a) Huang, T.; Keh, C. C. K.; Li, C.-J. Chem. Commun. 2002, 2440. (b) Yanada, R.; Nishimori, N.; Matsumura, A.; Fujii, N.; Takemoto, Y. Tetrahedron Lett. 2002, 43, 4585. (c) Jang, D. O.; Cho, D. H. Synlett 2002, 631.
33. Recently, three related indium-mediated radical reactions were reported. See: (a) Huang, T.; Keh, C. C. K.; Li, C.-J. Chem. Commun. 2002, 2440. (b) Yanada, R.; Nishimori, N.; Matsumura, A.; Fujii, N.; Takemoto, Y. Tetrahedron Lett. 2002, 43, 4585. (c) Jang, D. O.; Cho, D. H. Synlett 2002, 631.
34. Indium(I) iodide-mediated radical cyclization was recently studied. See: (a) Cook, G. R.; Erickson, S.; Hvinden, M. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC, 2001. Indium as a reducing agent, see: (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. Indium-mediated coupling reactions, see: (g) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727. (h) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
35. Indium(I) iodide-mediated radical cyclization was recently studied. See: (a) Cook, G. R.; Erickson, S.; Hvinden, M. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC, 2001. Indium as a reducing agent, see: (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. Indium-mediated coupling reactions, see: (g) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727. (h) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
36. Indium(I) iodide-mediated radical cyclization was recently studied. See: (a) Cook, G. R.; Erickson, S.; Hvinden, M. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC, 2001. Indium as a reducing agent, see: (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. Indium-mediated coupling reactions, see: (g) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727. (h) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
37. Indium(I) iodide-mediated radical cyclization was recently studied. See: (a) Cook, G. R.; Erickson, S.; Hvinden, M. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC, 2001. Indium as a reducing agent, see: (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. Indium-mediated coupling reactions, see: (g) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727. (h) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
38. Indium(I) iodide-mediated radical cyclization was recently studied. See: (a) Cook, G. R.; Erickson, S.; Hvinden, M. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC, 2001. Indium as a reducing agent, see: (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. Indium-mediated coupling reactions, see: (g) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727. (h) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
39. Indium(I) iodide-mediated radical cyclization was recently studied. See: (a) Cook, G. R.; Erickson, S.; Hvinden, M. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC, 2001. Indium as a reducing agent, see: (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. Indium-mediated coupling reactions, see: (g) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727. (h) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
40. Indium(I) iodide-mediated radical cyclization was recently studied. See: (a) Cook, G. R.; Erickson, S.; Hvinden, M. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC, 2001. Indium as a reducing agent, see: (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. Indium-mediated coupling reactions, see: (g) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727. (h) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
41. Indium(I) iodide-mediated radical cyclization was recently studied. See: (a) Cook, G. R.; Erickson, S.; Hvinden, M. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 1-5, 2001; American Chemical Society: Washington, DC, 2001. Indium as a reducing agent, see: (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. Chem. Commun. 1998, 2113. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem. Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385. Indium-mediated coupling reactions, see: (g) Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1991, 64, 727. (h) Ranu, B. C.; Dutta, P.; Sarkar, A. Tetrahedron Lett. 1998, 39, 9557.
42. For our reactions of imines in aqueous media, see: (a) Miyabe, H.; Ueda, M.; Naito, T. J. Org. Chem. 2000, 65, 5043. (b) Miyabe, H.; Ueda, M.; Naito, T. Chem. Commun. 2000, 2059. (c) Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6745.
43. For our reactions of imines in aqueous media, see: (a) Miyabe, H.; Ueda, M.; Naito, T. J. Org. Chem. 2000, 65, 5043. (b) Miyabe, H.; Ueda, M.; Naito, T. Chem. Commun. 2000, 2059. (c) Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6745.
44. For our reactions of imines in aqueous media, see: (a) Miyabe, H.; Ueda, M.; Naito, T. J. Org. Chem. 2000, 65, 5043. (b) Miyabe, H.; Ueda, M.; Naito, T. Chem. Commun. 2000, 2059. (c) Miyabe, H.; Yamaoka, Y.; Naito, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6745.
45. The configuration of major and minor products 2a, 5a, and 7a was determined by these NOESY spectra. See the Supporting Information.
46. For selected examples see: (a) Bailey, W. F.; Carson, M. W. J. Org. Chem. 1998, 63, 361. (b) Barluenga, J.; Sanz, R.; Fañanás, F. J. Tetrahedron Lett. 1997, 38, 2763. (c) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. (d) Coldham, I.; Hufton, R. Tetrahedron Lett. 1995, 36, 2157.
47. For selected examples see: (a) Bailey, W. F.; Carson, M. W. J. Org. Chem. 1998, 63, 361. (b) Barluenga, J.; Sanz, R.; Fañanás, F. J. Tetrahedron Lett. 1997, 38, 2763. (c) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. (d) Coldham, I.; Hufton, R. Tetrahedron Lett. 1995, 36, 2157.
48. For selected examples see: (a) Bailey, W. F.; Carson, M. W. J. Org. Chem. 1998, 63, 361. (b) Barluenga, J.; Sanz, R.; Fañanás, F. J. Tetrahedron Lett. 1997, 38, 2763. (c) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. (d) Coldham, I.; Hufton, R. Tetrahedron Lett. 1995, 36, 2157.
49. For selected examples see: (a) Bailey, W. F.; Carson, M. W. J. Org. Chem. 1998, 63, 361. (b) Barluenga, J.; Sanz, R.; Fañanás, F. J. Tetrahedron Lett. 1997, 38, 2763. (c) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. (d) Coldham, I.; Hufton, R. Tetrahedron Lett. 1995, 36, 2157.
50. Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. J. Chem. Soc., Perkin Trans. 1 1995, 19.
51. For the cyclization of radicals generated from α- halomethylsulfonamides, see: Leit, S. M.; Paquette, L. A. J. Org. Chem. 1999, 64, 9225.
52. (a) Greig, I. R.; Tozer, M. J.; Wright, P. T. Org. Lett. 2001, 3, 369.
53. (b) Martin, S. F.; Williamson, S. A.; Gist. R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170.
54. Sturino, C. F.; Fallis, A. G. J. Org. Chem. 1994, 59, 6514.