Diastereocontrol by a Hydroxyl Auxiliary in the Synthesis of Pyrrolidines via Radical Cyclization

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3023-3025

  Besev, Magnus ^a   Engman, Lars ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; FREE RADICAL; NITRILE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AZIRIDINES; CYCLIZATION; FREE RADICALS; NITRILES; PYRROLIDINES; STEREOISOMERISM;

EID: 0037026455     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026038t     Document Type: Article

References (41)

1. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie; Band E19a, C.-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301. Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol 1: Basic Principles, Vol 2: Applications.
2. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie; Band E19a, C.-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301. Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol 1: Basic Principles, Vol 2: Applications.
3. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie; Band E19a, C.-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301. Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol 1: Basic Principles, Vol 2: Applications.
4. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie; Band E19a, C.-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301. Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol 1: Basic Principles, Vol 2: Applications.
5. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie; Band E19a, C.-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301. Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol 1: Basic Principles, Vol 2: Applications.
6. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie; Band E19a, C.-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301. Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol 1: Basic Principles, Vol 2: Applications.
7. Giese, B. Radicals in Organic Synthesis: Formation of C-C bonds; Pergamon Press: Oxford, 1986. Regitz, M., Giese, B., Eds. Houben-Weyl, Methoden der Organishen Chemie; Band E19a, C.-Radikale, Teil 1+2; Georg Thieme Verlag: Stuttgart, 1989. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715 and 779. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301. Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001; Vol 1: Basic Principles, Vol 2: Applications.
8. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions - Concepts, Guidelines and Synthetic Applications; VCH: New York, 1996.
9. Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482. Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
10. Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482. Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
11. Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482. Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
12. Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482. Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
13. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
14. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
15. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
16. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
17. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
18. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
19. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
20. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
21. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
22. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
23. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés. C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poli, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenart-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
24. Ericsson, C.; Engman, L. Org. Lett. 2001, 3, 3459.
25. Besev, M., Engman, L. Org. Lett. 2000, 2, 1589.
26. For an example of hydrogen bonding in the synthesis of 2,3-disubstituted pyrrolidines, see: Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. See also: Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507. Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047.
27. For an example of hydrogen bonding in the synthesis of 2,3-disubstituted pyrrolidines, see: Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. See also: Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507. Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047.
28. For an example of hydrogen bonding in the synthesis of 2,3-disubstituted pyrrolidines, see: Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. See also: Hanessian, S.; Yang, H.; Schaum, R. J. Am. Chem. Soc. 1996, 118, 2507. Kündig, E. P.; Xu, L.-H.; Romanens, P. Tetrahedron Lett. 1995, 36, 4047.
29. US Pat. 4,321,197, 1983.
30. Deng, S. X.; Huang, D. W.; Landry, D. W. Tetrahedron Lett. 2001, 42, 6259. Sugimura, T.; Koguro, K.; Tai, A. Tetrahedron Lett. 1993, 34, 509. Apen, P. G.; Rasmussen, P. G. J. Heterocycl. Chem. 1992, 29, 1091. De Kimpe, N.; Sulmon, P.; Schamp, N. Bull. Soc. Chim. Belg. 1986, 95, 567. Fuerstner A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. Kao, K.-H.; Sheu, R.-S.; Chen, Y.-S.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Chem. Soc., Perkin Trans. 1 1999, 2383. Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061. Estieu, K.; Ollivier, J.; Salaun, J. Tetrahedron 1998, 54, 8075.
31. Deng, S. X.; Huang, D. W.; Landry, D. W. Tetrahedron Lett. 2001, 42, 6259. Sugimura, T.; Koguro, K.; Tai, A. Tetrahedron Lett. 1993, 34, 509. Apen, P. G.; Rasmussen, P. G. J. Heterocycl. Chem. 1992, 29, 1091. De Kimpe, N.; Sulmon, P.; Schamp, N. Bull. Soc. Chim. Belg. 1986, 95, 567. Fuerstner A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. Kao, K.-H.; Sheu, R.-S.; Chen, Y.-S.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Chem. Soc., Perkin Trans. 1 1999, 2383. Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061. Estieu, K.; Ollivier, J.; Salaun, J. Tetrahedron 1998, 54, 8075.
32. Deng, S. X.; Huang, D. W.; Landry, D. W. Tetrahedron Lett. 2001, 42, 6259. Sugimura, T.; Koguro, K.; Tai, A. Tetrahedron Lett. 1993, 34, 509. Apen, P. G.; Rasmussen, P. G. J. Heterocycl. Chem. 1992, 29, 1091. De Kimpe, N.; Sulmon, P.; Schamp, N. Bull. Soc. Chim. Belg. 1986, 95, 567. Fuerstner A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. Kao, K.-H.; Sheu, R.-S.; Chen, Y.-S.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Chem. Soc., Perkin Trans. 1 1999, 2383. Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061. Estieu, K.; Ollivier, J.; Salaun, J. Tetrahedron 1998, 54, 8075.
33. Deng, S. X.; Huang, D. W.; Landry, D. W. Tetrahedron Lett. 2001, 42, 6259. Sugimura, T.; Koguro, K.; Tai, A. Tetrahedron Lett. 1993, 34, 509. Apen, P. G.; Rasmussen, P. G. J. Heterocycl. Chem. 1992, 29, 1091. De Kimpe, N.; Sulmon, P.; Schamp, N. Bull. Soc. Chim. Belg. 1986, 95, 567. Fuerstner A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. Kao, K.-H.; Sheu, R.-S.; Chen, Y.-S.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Chem. Soc., Perkin Trans. 1 1999, 2383. Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061. Estieu, K.; Ollivier, J.; Salaun, J. Tetrahedron 1998, 54, 8075.
34. Deng, S. X.; Huang, D. W.; Landry, D. W. Tetrahedron Lett. 2001, 42, 6259. Sugimura, T.; Koguro, K.; Tai, A. Tetrahedron Lett. 1993, 34, 509. Apen, P. G.; Rasmussen, P. G. J. Heterocycl. Chem. 1992, 29, 1091. De Kimpe, N.; Sulmon, P.; Schamp, N. Bull. Soc. Chim. Belg. 1986, 95, 567. Fuerstner A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. Kao, K.-H.; Sheu, R.-S.; Chen, Y.-S.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Chem. Soc., Perkin Trans. 1 1999, 2383. Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061. Estieu, K.; Ollivier, J.; Salaun, J. Tetrahedron 1998, 54, 8075.
35. Deng, S. X.; Huang, D. W.; Landry, D. W. Tetrahedron Lett. 2001, 42, 6259. Sugimura, T.; Koguro, K.; Tai, A. Tetrahedron Lett. 1993, 34, 509. Apen, P. G.; Rasmussen, P. G. J. Heterocycl. Chem. 1992, 29, 1091. De Kimpe, N.; Sulmon, P.; Schamp, N. Bull. Soc. Chim. Belg. 1986, 95, 567. Fuerstner A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. Kao, K.-H.; Sheu, R.-S.; Chen, Y.-S.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Chem. Soc., Perkin Trans. 1 1999, 2383. Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061. Estieu, K.; Ollivier, J.; Salaun, J. Tetrahedron 1998, 54, 8075.
36. Deng, S. X.; Huang, D. W.; Landry, D. W. Tetrahedron Lett. 2001, 42, 6259. Sugimura, T.; Koguro, K.; Tai, A. Tetrahedron Lett. 1993, 34, 509. Apen, P. G.; Rasmussen, P. G. J. Heterocycl. Chem. 1992, 29, 1091. De Kimpe, N.; Sulmon, P.; Schamp, N. Bull. Soc. Chim. Belg. 1986, 95, 567. Fuerstner A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. Kao, K.-H.; Sheu, R.-S.; Chen, Y.-S.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Chem. Soc., Perkin Trans. 1 1999, 2383. Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061. Estieu, K.; Ollivier, J.; Salaun, J. Tetrahedron 1998, 54, 8075.
37. Deng, S. X.; Huang, D. W.; Landry, D. W. Tetrahedron Lett. 2001, 42, 6259. Sugimura, T.; Koguro, K.; Tai, A. Tetrahedron Lett. 1993, 34, 509. Apen, P. G.; Rasmussen, P. G. J. Heterocycl. Chem. 1992, 29, 1091. De Kimpe, N.; Sulmon, P.; Schamp, N. Bull. Soc. Chim. Belg. 1986, 95, 567. Fuerstner A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. Kao, K.-H.; Sheu, R.-S.; Chen, Y.-S.; Lin, W.-W.; Liu, J.-T.; Yao, C.-F. J. Chem. Soc., Perkin Trans. 1 1999, 2383. Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061. Estieu, K.; Ollivier, J.; Salaun, J. Tetrahedron 1998, 54, 8075.
38. Weiberth, F. J.; Hall, S. S. J. Org. Chem. 1987, 52, 3901.
39. Bartnik, R.; Laurent, A.; Lesniak, S. J. Chem. Res., Miniprint 1982, 2701.
40. Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323. See also ref 6.
41. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.