Remarkable Template Effect of a Lewis Acidic Receptor in Intramolecular Radical Cyclizations

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 11, 1997, Pages 1181-1183

  Ooi, Takashi ^a   Hokke, Yasutoshi ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Cyclizations; Lewis acids; Radical reactions; Template synthesis

Indexed keywords

EID: 0030838363     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199711811     Document Type: Article

References (28)

1. Reviews: a) B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, New York, 1986; b) D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications, VCH, Weinheim, 1996.
2. Reviews: a) B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon, New York, 1986; b) D. P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications, VCH, Weinheim, 1996.
3. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
4. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
5. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
6. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
7. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
8. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
9. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
10. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
11. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
12. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
13. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
14. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
15. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
16. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
17. Recent selected examples of stereoselective radical reactions influenced by Lewis acids: a) P. Renaud, M. Ribezzo, J. Am. Chem. Soc. 1991, 113, 7803; b) Y. Guindon, J.-F. Lavallee, M. Llinas-Brunet, G. Horner, J. Rancourt, ibid. 1991, 113, 9701; c) T. Toru, Y Watanabe, M. Tsusaka, Y. Ueno, J. Am. Chem. Soc. 1993, 115, 10464; d) P. Renaud, T. Bourquard, M. Gerster, N. Moufid, Angew. Chem. 1994, 106, 1680; Angew, Chem. Int. Ed. Engl. 1994, 33, 1601; e) Y. Yamamoto, S. Onuki, Y. Masatoshi, N. Asao, J. Am. Chem. Soc. 1994, 116, 421; f) M. Nishida, E. Ueyama, H. Hayashi, Y. Ohtake, Y. Yamaura, E. Yanaginuma, O. Yonemitsu, A. Nishida, N. Kawahara, ibid. 1994, 116, 6455; g) D. P. Curran, L. H. Kuo, J. Org. Chem. 1994, 59, 3259; h) P. Renaud, N. Moufid, L. H. Kuo, D. P. Curran, ibid. 1994, 59, 3547; i) H. Urabe, K. Yamashita, K. Suzuki, K. Kobayashi, F. Sato, ibid. 1995, 60, 3576; j) M. Murakata, H. Tsutsui, O. Hoshino, J. Chem. Soc. Chem. Commun. 1995, 481; k) M. P. Sibi, C. P. Jasperse, J. Ji, J. Am. Chem. Soc. 1995, 117, 10779; l) M. P. Sibi, J. Ji, Angew. Chem. 1996, 108, 198; Angew. Chem. Int. Ed. Engl. 1996, 35, 190; m) J. Am. Chem. Soc. 1996, 118, 3063.
18. For other synthetic applications of ATPH, see: a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, H. Imoto, H. Yamamoto, ibid. 1994, 116, 12115; c) K. Maruoka, M. Ito, H. Yamamoto, ibid. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928.
19. For other synthetic applications of ATPH, see: a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, H. Imoto, H. Yamamoto, ibid. 1994, 116, 12115; c) K. Maruoka, M. Ito, H. Yamamoto, ibid. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928.
20. For other synthetic applications of ATPH, see: a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, H. Imoto, H. Yamamoto, ibid. 1994, 116, 12115; c) K. Maruoka, M. Ito, H. Yamamoto, ibid. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928.
21. For other synthetic applications of ATPH, see: a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131; b) K. Maruoka, H. Imoto, H. Yamamoto, ibid. 1994, 116, 12115; c) K. Maruoka, M. Ito, H. Yamamoto, ibid. 1995, 117, 9091; d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 61, 2928.
22. The stereochemical assignment of the cyclization products 2 and 4 was made by independent syntheses, that is by the reduction of the corresponding stereochemically defined lactones, see: A. W. Murray, R. G. Reid, Synthesis, 1985, 35.
23. K. Nozaki, K. Oshima, K. Utimoto, J. Am. Chem. Soc. 1987, 109, 2547.
24. B. Giese, J. A. Gonzalez-Gomez, S. Lachhein, J. O. Metzger, Angew. Chem. 1987, 99, 475; Angew. Chem. Int. Ed. Engl. 1987, 26, 479.
25. B. Giese, J. A. Gonzalez-Gomez, S. Lachhein, J. O. Metzger, Angew. Chem. 1987, 99, 475; Angew. Chem. Int. Ed. Engl. 1987, 26, 479.
26. Attempted use of a catalytic amount of ATPH (0.2 equiv) for the radical cyclization of 3 in toluene at -78°C for 5 h gave rise to cyclic ether 4 (32%; E/Z = 40/60) and reduction product 5 (28%), and the starting material 3 was recovered in 37% yield.
27. For correlation of the stereochemistry of 2,3-disubstituted tetrahydrofurans such as 7, see: H. Frauenrath, T. Philipps, Liebigs Ann. Chem. 1985, 1951.
28. M. Journet, M. J. Malacria, J. Org. Chem. 1992, 57, 3085.