Radical cyclization of chiral N-(1-cycloalken-1-yl)-α-haloacetamides: Synthesis of optically active bicyclic pyrrolidinones

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2531-2538

  Ishibashi, Hiroyuki ^a,b   Fuke, Yumi ^a   Yamashita, Takashi ^a   Ikeda, Masazumi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDINONE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030249310     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00326-6     Document Type: Article

References (49)

1. 1. For reviews on the stereochemical control in radical addition and cyclization reactions, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969. RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
2. 1. For reviews on the stereochemical control in radical addition and cyclization reactions, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969. RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
3. 1. For reviews on the stereochemical control in radical addition and cyclization reactions, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969. RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
4. 1. For reviews on the stereochemical control in radical addition and cyclization reactions, see: Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969. RajanBabu, T.V. Acc. Chem. Res. 1991, 24, 139. Porter, N.A.; Giese, B.; Curran, D.P. Acc. Chem. Res. 1991, 24, 296. Smadja, W. Synlett 1994, 1.
5. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
6. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
7. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
8. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
9. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
10. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
11. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
12. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
13. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
14. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
15. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
16. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
17. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
18. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
19. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
20. 2. For recent references to the studies on controlling stereochemistry in radical addition and cyclization reactions, see: Thoma, G.; Curran, D.P.; Geib, S.V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc. 1993, 115, 8585. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. Giese, B.; Hoffmann, U.; Roth, M.; Velt, A.; Wyss, C.; Zehnder, M.; Zipse, H. Tetrahedron Lett. 1993, 34, 2445. Giese, B.; Damm, W.; Wetterich, F.; Zeltz, H.-G.; Rancourt, J.; Guindon, Y. Tetrahedron Lett. 1993, 34, 5885. Curran, D.P.; Sun, S. Tetrahedron Lett. 1993, 34, 6184. Curran, D.P.; Abraham, A.C. Tetrahedron 1993, 49, 4821. Curran, D.P.; Ramamoorthy, P.S. Tetrahedron 1993, 49, 4841. Beckwith, A.L.J.; Chai, C.L.L. Tetrahedron 1993, 49, 7871. Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421. Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35 1703. Renaud, P.; Bourquard, T. Tetrahedron Lett. 1994, 35, 1707. Ogura, K.; Kayano, A.; Sumitani, N.; Akazome, M.; Fujita, M. J. Org. Chem. 1995, 60, 1106. Morikawa, T.; Washio, Y.; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 271. Giese, B.; Bulliard, M.; Dickhaut, J.; Halbach, R.; Hassler, C.; Hoffmann, U.; Hinzen, B.; Senn, M. Synlett 1995, 116. Curran, D.P.; Balas, L. Synlett 1995, 119. Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W.W. Synlett 1995, 449. See also ref 3.
21. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
22. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
23. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
24. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
25. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
26. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
27. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
28. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
29. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
30. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
31. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
32. 3. Porter, N.A.; Lacher, B.; Chang, V.H.T.; Magnin, D.R. J. Am. Chem. Soc. 1989, 111, 8309. Curran, D.P.; Shen, W.; Zhang, J.; Heffner, T.A. J. Am. Chem. Soc. 1990, 112, 6738. Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315. Stack, J.G.; Curran, D.P.; Geib, S.V.; Rebek, Jr., J.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. Zahouily, M.; Journet, M.; Malacria, M. Synlett 1994, 366. Curran, D.P.; Shen, W.; Zhang, J.; Geib, S.V.; Lin, C.-H. Heterocycles, 1994, 37, 2315. Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663. Curran, D.P.; Geib, S.J.; Lin, C.-H. Tetrahedron Asymmetry 1994, 5, 199. Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455. Nishida, M.; Hayashi, H.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 269. Nishida, M.; Nobuta, M.; Nakaoka, K.; Nishida, A.; Kawahara, N. Tetrahedron Asymmetry 1995, 6, 2657. Nishida, M.; Hayashi, H.; Nishida, A.; Kawahara, N. J. Chem. Soc., Chem. Commun. 1996, 579.
33. 4. For a review on the carbamoylmethyl radical cyclizations, see Ishibashi, H.; Sato, T.; Ikeda, M. Yuki Gosei Kagaku Kyokai Shi 1995, 53, 85.
34. 5. For recent references, see (a) Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276.
35. (b) Sato, T.; Chono, N.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1995, 1115.
36. (c) Sato, T.; Kugo, Y.; Nakaumi, E.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1995, 1801.
37. (d) Ishibashi, H.; Kawanami, H.; Iriyama, H.; Ikeda, M. Tetrahedron Lett. 1995, 36, 6733.
38. (e) Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Synlett 1995, 912.
39. (f) Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Synlett 1995, 915.
40. (g) Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489.
41. 6. Ishibashi, H.; Nakamura, N.; Sato, T.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725. Sato, T.; Nakamura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1992, 2399.
42. 6. Ishibashi, H.; Nakamura, N.; Sato, T.; Takeuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725. Sato, T.; Nakamura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1992, 2399.
43. 7. The diastereoselectivity in other modes of cyclizations of chiral N-(1-phenylethyl)carbamoylmethyl radicals have been examined. For 5-exo-trig cyclizations of N-allylic systems, see (a) Cardillo, Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663.
44. (b) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M. Synlett 1995, 1159. For 4-exo-trig cyclizations of N-vinylic systems, see refs 5e, 5f and 5g.
45. 8. Omar, F.; Frahm, A.W. Arch. Pharm. (Weinheim) 1990, 323, 923.
46. 9. We thank a referee for helpful suggestion.
47. 10. Linz, W.; Xiang, J.-Z.; Becker, R.H.A.; Scholkens, B.A.; Unger, Th. Naunyn-Schmiedeberg's Arch. Pharmacol. 1983, 324 (Suppl.), R 42.
48. 3 solution with tetramethylsilane as an internal standard. For other general experimental details, see ref. 5a.
49. 12. Stork, G.; Mah, R. Heterocycles 1989, 28, 723.