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

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

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
Times cited : (26)

References (28)
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    • 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.
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    • 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.
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    • 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.
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    • Toru, T.1    Watanabe, Y.2    Tsusaka, M.3    Ueno, Y.4
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    • 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.
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    • Renaud, P.1    Bourquard, T.2    Gerster, M.3    Moufid, N.4
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    • 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.
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    • 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.
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    • Yamamoto, Y.1    Onuki, S.2    Masatoshi, Y.3    Asao, N.4
  • 9
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    • 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.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6455
    • Nishida, M.1    Ueyama, E.2    Hayashi, H.3    Ohtake, Y.4    Yamaura, Y.5    Yanaginuma, E.6    Yonemitsu, O.7    Nishida, A.8    Kawahara, N.9
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    • 0000457126 scopus 로고
    • 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.
    • (1994) J. Org. Chem. , vol.59 , pp. 3259
    • Curran, D.P.1    Kuo, L.H.2
  • 11
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    • 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.
    • (1994) J. Org. Chem. , vol.59 , pp. 3547
    • Renaud, P.1    Moufid, N.2    Kuo, L.H.3    Curran, D.P.4
  • 12
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    • 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.
    • (1995) J. Org. Chem. , vol.60 , pp. 3576
    • Urabe, H.1    Yamashita, K.2    Suzuki, K.3    Kobayashi, K.4    Sato, F.5
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    • 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.
    • (1995) J. Chem. Soc. Chem. Commun. , pp. 481
    • Murakata, M.1    Tsutsui, H.2    Hoshino, O.3
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    • 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.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10779
    • Sibi, M.P.1    Jasperse, C.P.2    Ji, J.3
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    • 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.
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    • 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.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 190
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    • 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.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3063
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    • 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.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4131
    • Maruoka, K.1    Imoto, H.2    Saito, S.3    Yamamoto, H.4
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    • 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.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 12115
    • Maruoka, K.1    Imoto, H.2    Yamamoto, H.3
  • 20
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    • 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.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9091
    • Maruoka, K.1    Ito, M.2    Yamamoto, H.3
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    • 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.
    • (1996) J. Org. Chem. , vol.61 , pp. 2928
    • Saito, S.1    Yamamoto, H.2
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    • 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.
    • (1985) Synthesis , pp. 35
    • Murray, A.W.1    Reid, R.G.2
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    • note
    • 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
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    • For correlation of the stereochemistry of 2,3-disubstituted tetrahydrofurans such as 7, see: H. Frauenrath, T. Philipps, Liebigs Ann. Chem. 1985, 1951.
    • (1985) Liebigs Ann. Chem. , pp. 1951
    • Frauenrath, H.1    Philipps, T.2


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