MgI2-mediated ring expansions of secondary methylenecyclopropyl amides

Journal of the American Chemical Society

Volumn 125, Issue 14, 2003, Pages 4028-4029

  Lautens, Mark ^a   Han, Wooseok ^a   Liu, Jack Hung Chang ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; MAGNESIUM DERIVATIVE; METHYLENECYCLOPROPYLAMIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037427333     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028967l     Document Type: Article

References (45)

1. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
2. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
3. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
4. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
5. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
6. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
7. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
8. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
9. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
10. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
11. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
12. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
13. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
14. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
15. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
16. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
17. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
18. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
19. For methylenecyclopropanes, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312. (b) Monti, H.; Rizzotto, D.; Léandri, G. Tetrahedron 1998, 54, 6725. (c) Yamago, S.; Nakamura, M.; Wang, X. Q.; Yanagawa, M.; Tokumitsu, S.; Nakamura, E. J. Org. Chem. 1998, 63, 1694. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (e) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77. (f) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1. For cyclopropanes, see: (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147. (h) Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876 and references therein. (i) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987. (j) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186. (k) Lee, P. H.; Lee, J. Tetrahedron Lett. 1998, 39, 7889 and references therein. (l) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp 946-947. (m) Ohta, T.; Takaya, H. In ref 11, Vol. 5, pp 1185-1205. (n) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66. (o) de Meijere, A. Angew. Chem., Int. Ed. Engl. 1979, 25, 1. (p) Stevens, R. V. Acc. Chem. Res. 1977, 10, 193. (q) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. For cyclopropenes, see: (r) Delgado, A.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3091. (s) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1984, 106, 805.
20. It is unusual that the amide nitrogen was incorporated instead of the carbonyl oxygen of the activating group (CONHQ) in these types of rearrangements. For a comparison see: Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 248 and ref 11.
21. The structure of 8ad was identified by X-ray crystallography.
22. The E-enolate should be a prerequisite for the product formation. Otherwise isomerization of double bond would be necessary.
23. For a review of synthesis of MCP derivatives, see: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
24. For a review of synthesis of N-sulfonyl imines, see: Weinreb, S. M. Top. Curr. Chem. 1997, 190, 131.
25. Interestingly, only trans-methylenepyrrolidine 2dd was isolated in 31%.
26. For recent examples of chelation effect of pyrid-2-yl group, see: (a) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (b) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (c) Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600. (d) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (e) Itami, K.; Mitsudo, K.; Kamei, T.; Koike, T.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2000, 122, 12013. (f) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
27. For recent examples of chelation effect of pyrid-2-yl group, see: (a) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (b) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (c) Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600. (d) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (e) Itami, K.; Mitsudo, K.; Kamei, T.; Koike, T.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2000, 122, 12013. (f) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
28. For recent examples of chelation effect of pyrid-2-yl group, see: (a) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (b) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (c) Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600. (d) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (e) Itami, K.; Mitsudo, K.; Kamei, T.; Koike, T.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2000, 122, 12013. (f) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
29. For recent examples of chelation effect of pyrid-2-yl group, see: (a) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (b) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (c) Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600. (d) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (e) Itami, K.; Mitsudo, K.; Kamei, T.; Koike, T.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2000, 122, 12013. (f) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
30. For recent examples of chelation effect of pyrid-2-yl group, see: (a) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (b) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (c) Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600. (d) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (e) Itami, K.; Mitsudo, K.; Kamei, T.; Koike, T.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2000, 122, 12013. (f) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
31. For recent examples of chelation effect of pyrid-2-yl group, see: (a) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (b) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (c) Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600. (d) Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663. (e) Itami, K.; Mitsudo, K.; Kamei, T.; Koike, T.; Nokami, T.; Yoshida, J.-i. J. Am. Chem. Soc. 2000, 122, 12013. (f) Paquette, L. A.; Rothhaar, R. R. J. Org. Chem. 1999, 64, 217.
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40. (b) Jones, R. C. F.; Patience, J. M. J. Chem. Soc., Perkin Trans. 1 1990, 2350.
41. For recent reviews of the corresponding silyloxy derivatives, see: (c) Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221.
42. (d) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
43. (e) Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Chem. Soc. Rev. 2000, 29, 109.
44. The relative stereochemistry for the major diastereomer was proven to be anti by X-ray crystallography.
45. de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Top. Curr. Chem. 2000, 207, 89.