Sulfur-Directed Asymmetric 1,3-Dipolar Cycloadditions of Azomethine Ylides with Enantiopure Sulfinimines

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2316-2317

  Viso, Alma ^a   De la Pradilla, Roberto Fernández ^b   Guerrero Strachan, Carlos ^b   Alonso, Marta ^b   Martínez Ripoll, Martín ^c   André, Isabelle ^c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000030326     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970005n     Document Type: Article

References (39)

1. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984.
2. For a review, see: Tsuge, O.; Kanemasa, S. Adv. Heterocycl. Chem. 1989, 45, 231-349.
3. For leading references, see: (a) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (b) Waldmann, H.; Bläser, E.; Jansen, M.; Letschert, H.-P. Chem. Eur. J. 1995, 1, 150-154. (c) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475-2486.
4. For leading references, see: (a) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (b) Waldmann, H.; Bläser, E.; Jansen, M.; Letschert, H.-P. Chem. Eur. J. 1995, 1, 150-154. (c) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475-2486.
5. For leading references, see: (a) Galley, G.; Liebscher, J.; Pätzel, M. J. Org. Chem. 1995, 60, 5005-5010. (b) Waldmann, H.; Bläser, E.; Jansen, M.; Letschert, H.-P. Chem. Eur. J. 1995, 1, 150-154. (c) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475-2486.
6. (a) Lown, J. W. In ref 1, Vol. 1, pp 653-732.
7. (b) Bende, Z.; Bitter, I.; Toke, L.; Weber, L.;. Toth, G.; Janke, F. Liebigs. Ann. Chem. 1982, 2146-2152.
8. (c) Grigg, R.; Donegan, G.; Gunaratne, H. Q. N.; Kennedy, D. A.; Malone, J. F.; Sridharan, V.; Thianpatanagul, S. Tetrahedron 1989, 45, 1723-1746.
9. (d) Amornraksa, K.; Barr, D.; Donegan, G.; Grigg, R.; Ratananukul, P.; Sridharan, V. Ibid. 1989, 45, 4649-4668.
10. (e) Lerestif, J. M.; Bazureau, J. P.; Hamelin, J. Tetrahedron Lett. 1993, 29, 4639-4642.
11. (f) Padwa, A.; Dean, D. C.; Osterhout, H.; Precedo, L.; Semones, M. A. J. Org. Chem. 1994, 59, 5347-5357.
12. (g) Nagao, Y.; Kim, K.; Komaki, Y.; Sano, S.; Kihara, M.; Shiro, M. Heterocycles 1994, 38, 587-593.
13. For leading references, see: (a) Alexakis, A.; Lensen, N.; Tranchier, J.-P.; Mangeney, P.; Feneu-Dupont, J.; Declercq, J.-P. Synthesis 1995, 1038-1050. (b) Alexakis, A.; Tranchier, J.-P.; Lensen, N.; Mangeney, P. J. Am. Chem. Soc. 1995, 117, 10767-10768.
14. For leading references, see: (a) Alexakis, A.; Lensen, N.; Tranchier, J.-P.; Mangeney, P.; Feneu-Dupont, J.; Declercq, J.-P. Synthesis 1995, 1038-1050. (b) Alexakis, A.; Tranchier, J.-P.; Lensen, N.; Mangeney, P. J. Am. Chem. Soc. 1995, 117, 10767-10768.
15. For leading references, see: (a) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229-6232. (b) Yang, T.-K.; Chen, R.-Y,; Lee, D.-S.; Peng, W.-S.; Jiang, Y.-Z.; Mi, A.-Q.; Jong, T.-T. J. Org. Chem. 1994, 59, 914-921 and references cited therein.
16. For leading references, see: (a) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229-6232. (b) Yang, T.-K.; Chen, R.-Y,; Lee, D.-S.; Peng, W.-S.; Jiang, Y.-Z.; Mi, A.-Q.; Jong, T.-T. J. Org. Chem. 1994, 59, 914-921 and references cited therein.
17. For leading references, see: (a) Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222-2225. (b) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. Ibid. 1996, 61, 440-441. (c) Hose, D. R. J.; Mahon, M. F.; Molloy, K. C.; Raynham, T.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 691-703. (d) García Ruano, J. L.; Fernández, I.; del Prado Catalina, M.; Alcudia Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414. (e) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881-3884. (f) Balasubramanian, T.; Hassner, A. Ibid. 1996, 37, 5755-5758.
18. For leading references, see: (a) Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222-2225. (b) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. Ibid. 1996, 61, 440-441. (c) Hose, D. R. J.; Mahon, M. F.; Molloy, K. C.; Raynham, T.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 691-703. (d) García Ruano, J. L.; Fernández, I.; del Prado Catalina, M.; Alcudia Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414. (e) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881-3884. (f) Balasubramanian, T.; Hassner, A. Ibid. 1996, 37, 5755-5758.
19. For leading references, see: (a) Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222-2225. (b) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. Ibid. 1996, 61, 440-441. (c) Hose, D. R. J.; Mahon, M. F.; Molloy, K. C.; Raynham, T.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 691-703. (d) García Ruano, J. L.; Fernández, I.; del Prado Catalina, M.; Alcudia Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414. (e) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881-3884. (f) Balasubramanian, T.; Hassner, A. Ibid. 1996, 37, 5755-5758.
20. For leading references, see: (a) Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222-2225. (b) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. Ibid. 1996, 61, 440-441. (c) Hose, D. R. J.; Mahon, M. F.; Molloy, K. C.; Raynham, T.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 691-703. (d) García Ruano, J. L.; Fernández, I.; del Prado Catalina, M.; Alcudia Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414. (e) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881-3884. (f) Balasubramanian, T.; Hassner, A. Ibid. 1996, 37, 5755-5758.
21. For leading references, see: (a) Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222-2225. (b) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. Ibid. 1996, 61, 440-441. (c) Hose, D. R. J.; Mahon, M. F.; Molloy, K. C.; Raynham, T.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 691-703. (d) García Ruano, J. L.; Fernández, I.; del Prado Catalina, M.; Alcudia Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414. (e) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881-3884. (f) Balasubramanian, T.; Hassner, A. Ibid. 1996, 37, 5755-5758.
22. For leading references, see: (a) Davis, F. A.; Szewczyk, J. M.; Reddy, R. E. J. Org. Chem. 1996, 61, 2222-2225. (b) Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. Ibid. 1996, 61, 440-441. (c) Hose, D. R. J.; Mahon, M. F.; Molloy, K. C.; Raynham, T.; Wills, M. J. Chem. Soc., Perkin Trans. 1 1996, 691-703. (d) García Ruano, J. L.; Fernández, I.; del Prado Catalina, M.; Alcudia Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407-3414. (e) Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881-3884. (f) Balasubramanian, T.; Hassner, A. Ibid. 1996, 37, 5755-5758.
23. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60, 7037-7039.
24. (a) Marino, J. P.; Viso, A.; Fernández de la Pradilla, R.; Fernández, P. J. Org. Chem. 1991, 56, 1349-1351.
25. (b) Arjona, O.; Fernández de la Pradilla, R.; Mallo, A.; Plumet, J.; Viso, A. Tetrahedron Lett. 1990, 31, 1475-1478.
26. (c) Fernández de la Pradilla, R.; Castro, S.; Manzano, P.; Priego, J.; Viso, A. J. Org. Chem. 1996, 61, 3586-3587.
27. Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481 and previous papers from this group.
28. All new products were fully characterized by standard techniques.
29. Sulfinimine 2 was prepared in one step from p-nitrobenzaldehyde by the procedure of Davis (ref 6a).
30. -3. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ. UK.
31. -3. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ. UK.
32. -3. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ. UK.
33. Mikolajczyk, M.; Drabowicz, J.; Bujnicki, B. J. Chem. Soc., Chem. Commun. 1976, 568-569.
34. We found this reduction to be very sluggish presumably due to the carboxylate being very hindered. Short reaction times resulted in recovery of starting material. Intermediate reaction times (5 h) afforded mixtures of 15 and the expected sulfmamide, whose treatment with TFA/MeOH also led to diamine 16. We are examining other procedures to carry out the selective reduction of the ester.
35. Vicinal diamines are important chiral auxiliaries. For a review, see: Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. For a leading reference see: Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386-2388. For leading references on synthesis of vicinal diamines, see: (a) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 36, 9241-9244. (b) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607-8610. (c) Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757-3758.
36. Vicinal diamines are important chiral auxiliaries. For a review, see: Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. For a leading reference see: Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386-2388. For leading references on synthesis of vicinal diamines, see: (a) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 36, 9241-9244. (b) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607-8610. (c) Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757-3758.
37. Vicinal diamines are important chiral auxiliaries. For a review, see: Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. For a leading reference see: Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386-2388. For leading references on synthesis of vicinal diamines, see: (a) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 36, 9241-9244. (b) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607-8610. (c) Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757-3758.
38. Vicinal diamines are important chiral auxiliaries. For a review, see: Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. For a leading reference see: Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386-2388. For leading references on synthesis of vicinal diamines, see: (a) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 36, 9241-9244. (b) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607-8610. (c) Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757-3758.
39. Vicinal diamines are important chiral auxiliaries. For a review, see: Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526. For a leading reference see: Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386-2388. For leading references on synthesis of vicinal diamines, see: (a) Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett. 1995, 36, 9241-9244. (b) Shimizu, M.; Kamei, M.; Fujisawa, T. Tetrahedron Lett. 1995, 36, 8607-8610. (c) Park, Y. S.; Boys, M. L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757-3758.