Stereoselcctivity in reactions of 1,2-dioxy-substituted radicals under chelation control: An unexpected result

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 20, 1996, Pages 2396-2399

  Gerster, Michèle ^a   Schenk, Kurt ^b   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Asymmetric induction; Chelate control; Diols; Hydrostannylations; Radicals

Indexed keywords

EID: 0030445423     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199623961     Document Type: Article

References (41)

1. P. Renaud, M. Gerster, J. Am. Chem. Soc. 1995, 117, 6607-6608.
2. 3 to prepare the aluminum alkoxide.
3. Reviews on the stereoselectivity of radical reactions: N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 296-304; W. Smadja, Synlett 1994, 1-26; D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
4. Reviews on the stereoselectivity of radical reactions: N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 296-304; W. Smadja, Synlett 1994, 1-26; D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
5. Reviews on the stereoselectivity of radical reactions: N. A. Porter, B. Giese, D. P. Curran, Acc. Chem. Res. 1991, 24, 296-304; W. Smadja, Synlett 1994, 1-26; D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996.
6. For stereoselective reactions based on 1-oxy radicals, see: B. Giese, W. Damm, J. Dickhaut, F. Wetterich, S. Sun, D. P. Curran, Tetrahedron Lett. 1991, 32, 6097-6100; B. Giese, B. Carboni, T. Göbel, R. Muhn, F. Wetterich, ibid. 1992, 33, 2673-2676.
7. For stereoselective reactions based on 1-oxy radicals, see: B. Giese, W. Damm, J. Dickhaut, F. Wetterich, S. Sun, D. P. Curran, Tetrahedron Lett. 1991, 32, 6097-6100; B. Giese, B. Carboni, T. Göbel, R. Muhn, F. Wetterich, ibid. 1992, 33, 2673-2676.
8. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
9. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
10. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
11. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
12. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
13. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
14. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
15. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
16. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
17. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
18. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
19. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
20. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
21. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
22. For chelation control in radical reactions, see: Y. Guindon, J.-F. Lavallée, M. Llinas-Brunet, G. Horner, J. Rancourt, J. Am. Chem. Soc. 1991, 113, 9701-9702; Y. Guindon, B. Guérin, C. Chabot, N. Mackintosh, W. W. Ogilvie, Synlett 1995, 449-451; H. Nagano, Y. Kuno, J. Chem. Soc. Chem. Commun. 1994, 987-988; T. Toru, Y. Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464-10465; M. Kito, T. Sakai, K. Yamada, F. Matsuda, H. Shiramana, Synlett 1993, 158-162; T. Gillmann, Tetrahedron Lett. 1993, 34, 607-610; Y. Yamamoto, S. Onuki, M. Yumoto, N. Asao, J. Am. Chem. Soc. 1994, 116, 421-422; M. Kawatsura. F. Matsuda, H. Shirahama, J. Org. Chem. 1994, 59, 6900-6901; A. G. Molander, J. A. McKie, ibid. 1995, 60, 872-882; H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576-3577; J. Hongliu, R. Radinov, N. A. Porter, J. Am. Chem. Soc. 1995, 117, 11029-11030; M. P. Sibi, C. J. Jasperse, J. Ji, ibid. 1995, 117, 10779-10780; H. Stadtmüller, P. Knochel, Synlett 1995, 463-464. M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198-200; Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
23. K. S. Feldman, H. M. Berven, P. H. Weinreb, J. Am. Chem. Soc. 1993, 115, 11364-11369.
24. R. N. Saisic, R. Matovic, Z. Cekovic, Gazz. Chim. Ital. 1991, 121, 325-328.
25. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-89. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code + (1223) 336-033; e-mail: teched@chemcrys.cam.ac.uk).
26. 13C NMR study supports the formation of a chelate. Details will be published in a forthcoming full paper.
27. The reaction with like(lk) topicity affords the unlike(u) product and vice versa.
28. J. E. Eksterowicz, K. N. Houk, Tetrahedron Lett. 1993, 34, 427-430; W. Damm, J. Dickhaut, F. Wetterich, B. Giese, ibid. 1993, 34, 431-434.
29. J. E. Eksterowicz, K. N. Houk, Tetrahedron Lett. 1993, 34, 427-430; W. Damm, J. Dickhaut, F. Wetterich, B. Giese, ibid. 1993, 34, 431-434.
30. R. D. McKelvey, T. Sugarawa, H. Iwamura, Magn. Reson. Chem. 1985, 23, 330-334; Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 1992, 114, 1656-1661.
31. R. D. McKelvey, T. Sugarawa, H. Iwamura, Magn. Reson. Chem. 1985, 23, 330-334; Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 1992, 114, 1656-1661.
32. Very recently it was found that the stereoselectivity of 1-amino-substituted cyclic radicals was strongly dependent of the nature of the R group attached at the radical center. An explanation based on pyramidalization of the reactive center in the transition state was proposed: D. Crich, S. Natarajan, J. Org. Chem. 1995, 60, 6237-6241.
33. D. J. Cram, F. A. A. Elhafez, J. Am. Chem. Soc. 1952, 74, 5828-5835; D. J. Cram, K. R. Kopecky, ibid. 1959, 81, 2748-2755; D. J. Cram, D. R. Wilson, ibid. 1963, 85, 1245-1249; J. H. Stocker, P. Sidisunthorn, B. M. Benjamin, C. J. Collins, ibid. 1960, 82, 3913-3918; for a review, see: E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
34. D. J. Cram, F. A. A. Elhafez, J. Am. Chem. Soc. 1952, 74, 5828-5835; D. J. Cram, K. R. Kopecky, ibid. 1959, 81, 2748-2755; D. J. Cram, D. R. Wilson, ibid. 1963, 85, 1245-1249; J. H. Stocker, P. Sidisunthorn, B. M. Benjamin, C. J. Collins, ibid. 1960, 82, 3913-3918; for a review, see: E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
35. D. J. Cram, F. A. A. Elhafez, J. Am. Chem. Soc. 1952, 74, 5828-5835; D. J. Cram, K. R. Kopecky, ibid. 1959, 81, 2748-2755; D. J. Cram, D. R. Wilson, ibid. 1963, 85, 1245-1249; J. H. Stocker, P. Sidisunthorn, B. M. Benjamin, C. J. Collins, ibid. 1960, 82, 3913-3918; for a review, see: E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
36. D. J. Cram, F. A. A. Elhafez, J. Am. Chem. Soc. 1952, 74, 5828-5835; D. J. Cram, K. R. Kopecky, ibid. 1959, 81, 2748-2755; D. J. Cram, D. R. Wilson, ibid. 1963, 85, 1245-1249; J. H. Stocker, P. Sidisunthorn, B. M. Benjamin, C. J. Collins, ibid. 1960, 82, 3913-3918; for a review, see: E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
37. D. J. Cram, F. A. A. Elhafez, J. Am. Chem. Soc. 1952, 74, 5828-5835; D. J. Cram, K. R. Kopecky, ibid. 1959, 81, 2748-2755; D. J. Cram, D. R. Wilson, ibid. 1963, 85, 1245-1249; J. H. Stocker, P. Sidisunthorn, B. M. Benjamin, C. J. Collins, ibid. 1960, 82, 3913-3918; for a review, see: E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
38. Preliminary experiments have shown that the 2-tert-butyl-l-methyloxiranyl radical reacts preferentially with til topicity that is syn to the tert-butyl group. For reaction with monosubstituted oxiranyl radicals, see: F. E. Ziegler, P. G. Harran, Tetrahedron Lett. 1993, 34, 4505-4508.
39. Syn bromination of 2-substituted aziridinyl radicals has been reported: F. E. Ziegler, M. Belena, J. Org. Chem. 1994, 59, 7962-7967.
40. For a recent result that may fit in this category, see: H. Urabe, K. Kobayashi, F. Sato, J. Chem. Soc. Chem. Commun. 1995, 1043-1044. See also J. O. Metzger, K. Schwarzkopf, W. Saak, S. Pohl, Chem. Ber. 1994, 127, 1069-1073.
41. For a recent result that may fit in this category, see: H. Urabe, K. Kobayashi, F. Sato, J. Chem. Soc. Chem. Commun. 1995, 1043-1044. See also J. O. Metzger, K. Schwarzkopf, W. Saak, S. Pohl, Chem. Ber. 1994, 127, 1069-1073.