Diastereoselective and Enantioselective Intramolecular Amino-Zinc-Enolate Carbometalation Reactions. A New Polysubstituted Pyrrolidines Synthesis

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2442-2450

  Lorthiois, Edwige ^a   Marek, Ilane ^a   Normant, Jean F ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000541846     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970813e     Document Type: Article

References (55)

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15. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
16. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
17. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
18. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
19. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
20. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
21. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
22. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
23. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
24. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
25. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
26. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
27. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
28. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
29. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
30. For the more recent publications on the synthesis of pyrrolidines via an anionic cyclization, see: (a) Fujita, H.; Tokuda, M.; Nitta, M.; Suginome, H. Tetrahedron Lett. 1992, 33, 6359-6362. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (c) Coldham, I. J. Chem. Soc., Perkin Trans. 1 1993, 1275-1276. (d) Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 7001-7004. (e) Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662-5671. (f) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (g) Coldham, I.; Hugton, R. Tetrahedron Lett. 1995, 36, 2157-2160. (h) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 7, 12336-12337. (i) Barluenga, J.; Canteli, R. M.; Florez, J. J. Org. Chem. 1996, 61, 3753-3757. (j) Solé, D.; Cancho, Y.; Llebaria, A.; Moreto, J.; Delgado, A. J. Org. Chem. 1996, 61, 5895-5904. For a palladium-mediated cyclization, see: Van der Louw, J.; Van der Baan, J. L.; Stichter, H.; Out, G. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1988, 29, 3579-3580. For the more recent publications on the synthesis of 3-substituted pyrrolidines via a cyclization of carbon-centered glycine radicals, see: (a) Each, P. M.; Hiemstra, H.; De Boer, R. P.; Speckamp, W. N. Tetrahedron 1992, 48, 4659-4676. (b) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1994, 50, 1907-1918 and references therein, (c) Schulze, R.; Backhaus, H. D.; Rüchardt, C. Chem. Ber. 1993, 126, 1031. (d) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841. (e) Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2887-2890.
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45. 19 with the Wittig reagent, and reaction of the secondary amine with the α-bromoester as previously described in Scheme 4.
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50. Reaction of butadiene with HBrO: Masuda, H.; Takase, K.; Nishio, M.; Hasegawa, A.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1994, 59, 5550-5555. Protection of the alcool moiety into the methoxy methyl derivative: Gras, J. L.; Ko Win Chan, Y.; Guerin, A. Synthesis 1985, 74-75. For alkylation of this latter with the amino derivative, see ref 10.
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55. In the match pair, the two substituents will be in the pseudoequatorial positions.