Radical cyclization approach to synthesis of enantiopure proline derivatives

Synlett

Volumn , Issue 7, 2003, Pages 1058-1060

  Agami, Claude ^a   Comesse, Sébastien ^a   Guesné, Sébastien ^a   Kadouri Puchot, Catherine ^a   Martinon, Luc ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Diastereoselective radical cyclization; Proline derivatives; amino alcohols

Indexed keywords

AMINOALCOHOL; PROLINE DERIVATIVE; SILANE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0037899655     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39289     Document Type: Article

References (43)

1. (a) Giese, B.; Kopping, B.; Göbel, T.; Dickaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
2. (b) Curran, D. P. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991, 779.
3. (c) Jasperse, P.; Curran, D. P.; Fevig, T. L. Chem Rev 1991, 91, 1237.
4. (d) Aldabbagh, F.; Bowman, W. R. Contemp. Org. Synth. 1997, 261.
5. (e) Bowman, W. R.; Bridge, C. F.; Brookes, P. J. Chem. Soc. Perkin Trans 1 2000, 1.
6. (f) Bowman, W. R.; Cloonan, M. O.; Krintel, S. L. J. Chem. Soc. Perkin Trans 1 2001, 2885; and references cited therein.
7. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
8. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
9. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
10. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
11. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
12. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
13. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
14. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
15. For recent examples of synthesis of pyrrolidines via a radical cyclization, see: (a) Besev, M.; Engman, L. Org. Lett. 2000, 2, 1589. (b) Besev, M.; Engman, L. Org. Lett. 2002, 4, 3023. (c) Rancourt, J.; Gorys, V.; Jolicoeur, E. Tetrahedron Lett. 1998, 39, 5339. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. (e) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. (f) Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. (g) Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Mendiguchia, P. Eur. J. Org. Chem. 2000, 3727. (h) Lee, E.; Kim, S. K.; Kim, J. Y.; Lim, J. Tetrahedron Lett. 2000, 41, 5915. (i) Suero, R.; Gorgojo, J. M.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6211.
16. (a) Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc. Perkin Trans. 1 1991, 2885.
17. (b) Adlington, R. M.; Mantell, S. J. Tetrahedron 1992, 48, 6529.
18. (c) Basak, A.; Bag, S. S.; Rudra, K. R.; Barman, J.; Dutta, S. Chemistry Lett. 2002, 710.
19. (d) Bowman, W. R.; Broadhurst, M. J.; Coghlan, D. R.; Lewis, K. A. Tetrahedron Lett. 1997, 38, 6301.
20. (e) Esh, P. M.; Hiemstra, H.; de Boer, R. F.; Speckamp, W. N. Tetrahedron 1992, 48, 4659.
21. (f) Osipov, S. N.; Burger, K. Tetrahedron Lett. 2000, 41, 5659.
22. (g) Bryans, J. S.; Large, J. M.; Parsons, A. F. J. Chem. Soc. Perkin Trans. 1 1999, 2905.
23. (h) Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Chem. Commun. 1994, 1383.
24. Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 1496.
25. Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424.
26. See, for example: (a) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc. Perkin Trans. 2 1992, 857. (b) Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959. (c) Kano, S.; Yuasa, Y.; Moshizuki, N.; Shibuya, S. Heterocycles 1990, 30, 263. (d) Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1984, 106, 8209.
27. See, for example: (a) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc. Perkin Trans. 2 1992, 857. (b) Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959. (c) Kano, S.; Yuasa, Y.; Moshizuki, N.; Shibuya, S. Heterocycles 1990, 30, 263. (d) Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1984, 106, 8209.
28. See, for example: (a) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc. Perkin Trans. 2 1992, 857. (b) Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959. (c) Kano, S.; Yuasa, Y.; Moshizuki, N.; Shibuya, S. Heterocycles 1990, 30, 263. (d) Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1984, 106, 8209.
29. See, for example: (a) Udding, J. H.; Tuijp, C. J. M.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc. Perkin Trans. 2 1992, 857. (b) Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959. (c) Kano, S.; Yuasa, Y.; Moshizuki, N.; Shibuya, S. Heterocycles 1990, 30, 263. (d) Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1984, 106, 8209.
30. (a) Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1988, 53, 3641.
31. (b) Ballestri, M.; Chatgilialoglu, C.; Clark, K. B.; Griller, D.; Giese, B.; Kopping, B. J. Org. Chem. 1991, 56, 678.
32. 3).
33. 1H NMR on the crude mixture.
34. Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron 1989, 45, 923.
35. 2O/cyclohexane, 10:90) afforded compound 9 (15 mg, 40% yield)
36. Baldwin, J. E. J. Chem. Soc. Chem. Commun. 1976, 734.
37. The proposal of a chair conformation for the morpholinone template has been proposed previously and backed up by theoretical calculations, see: (a) Harwood, M. L.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537. (b) Drew, M. G. B.; Harwood, L. M.; Price, D. W.; Choi, M.-S.; Park, G. Tetrahedron Lett. 2000, 41, 5077.
38. The proposal of a chair conformation for the morpholinone template has been proposed previously and backed up by theoretical calculations, see: (a) Harwood, M. L.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537. (b) Drew, M. G. B.; Harwood, L. M.; Price, D. W.; Choi, M.-S.; Park, G. Tetrahedron Lett. 2000, 41, 5077.
39. (a) Beckwith, A. L. J.; Easton, C. J.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 482.
40. (b) Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc. Chem., Commun. 1980, 484.
41. (c) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
42. Aldous, D. J.; Drew, M. G. B.; Hamelin, E. M. N.; Harwood, L. M.; Jahans, A. B.; Thurairatman, S. Synlett 2001, 1836.
43. 3).