Aza-Darzens asymmetric synthesis of N-(p-toluenesulfinyl)aziridine 2- carboxylate esters from sulfinimines (N-sulfinyl imines)

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7559-7567

  Davis, Franklin A ^a   Liu, Hu ^a   Zhou, Ping ^b   Fang, Tianan ^a   Reddy, G Venkat ^a   Zhang, Yulian ^a  

^a Temple University   (United States)

^b DREXEL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; N (TOLUENESULFINYL)AZIRIDINE 2 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS; UNITED STATES;

EID: 0033215072     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990907j     Document Type: Article

References (51)

1. For reviews of aziridines, see (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (b) Pearson, W. H.; Lian, B. W. Aziridines and Azirines: Monocyclic. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: Oxford, 1996; Vol. 1A, Chapter 1, p 1. (c) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
2. For reviews of aziridines, see (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (b) Pearson, W. H.; Lian, B. W. Aziridines and Azirines: Monocyclic. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: Oxford, 1996; Vol. 1A, Chapter 1, p 1. (c) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
3. For reviews of aziridines, see (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (b) Pearson, W. H.; Lian, B. W. Aziridines and Azirines: Monocyclic. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: Oxford, 1996; Vol. 1A, Chapter 1, p 1. (c) Atkinson, R. S. Tetrahedron 1999, 55, 1519.
4. For leading references, see (a) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Fujii, N.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 652. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982.
5. For leading references, see (a) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Fujii, N.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 652. (b) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2982.
6. Ibuka, T.; Nakai, K.; Akaji, M.; Mimura, N.; Ohno, H.; Tamamura, Fujii, N. Tetrahedron 1996, 52, 11739.
7. Andereson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364.
8. Willems, J. G. H.; Dommerholt, F. J.; Hammink, J. B.; Vaarhost, A. M.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 603.
9. For a review, see Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
10. For leading references, see Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243.
11. Antilla, J. C.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 5099.
12. (a) Davis, F. A.; Reddy, G. V.; Liang, C.-H. Tetrahedron Lett. 1997, 35, 5139.
13. (b) Davis, F. A.; Liu, H.; Reddy, G. V. Tetrahedron Lett. 1986, 37, 5473.
14. Davis, F. A.; Liang, C.-H.; Liu, H. J. Org. Chem. 1997, 62, 3796.
15. Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525.
16. Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349.
17. Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651.
18. For Darzens-type synthesis of racemic aziridines, see Rosen, T. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 409. Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121.
19. For Darzens-type synthesis of racemic aziridines, see Rosen, T. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 409. Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121.
20. Davis, F. A.; Zhou, P.; Liang, C.-H.; Reddy, R. E. Tetrahedron: Asymmetry 1995, 6, 1511.
21. Ruano, J. L. G.; Fernandez, I.; Catalina, M.; Cruz, A. A. Tetrahedron: Asymmetry 1996, 7, 3407.
22. Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249.
23. (a) Maryanoff, C. A.; Sorgi, K. L.; Zientek, A. M. J. Org. Chem. 1994, 59, 237.
24. (b) Fujisawa, T.; Hayakawa, R.; Shimizu, M. Tetrahedron Lett. 1992, 33, 7903.
25. (c) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121.
26. For examples of this technique, see (a) Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. (b) Campell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. (c) Singer, R. A.; Carreria, E. M. Tetrahedron Lett. 1997, 38, 927. (d) For a review, see D'Angelo, J. Tetrahedron 1976, 32, 2979.
27. For examples of this technique, see (a) Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. (b) Campell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. (c) Singer, R. A.; Carreria, E. M. Tetrahedron Lett. 1997, 38, 927. (d) For a review, see D'Angelo, J. Tetrahedron 1976, 32, 2979.
28. For examples of this technique, see (a) Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. (b) Campell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. (c) Singer, R. A.; Carreria, E. M. Tetrahedron Lett. 1997, 38, 927. (d) For a review, see D'Angelo, J. Tetrahedron 1976, 32, 2979.
29. For examples of this technique, see (a) Mori, Y.; Yaegashi, K.; Iwase, K.; Yamamori, Y.; Furukawa, H. Tetrahedron Lett. 1996, 37, 2605. (b) Campell, J. B.; Dedinas, R. F.; Trumbower-Walsh, S. A. J. Org. Chem. 1996, 61, 6205. (c) Singer, R. A.; Carreria, E. M. Tetrahedron Lett. 1997, 38, 927. (d) For a review, see D'Angelo, J. Tetrahedron 1976, 32, 2979.
30. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, T. R.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2, 2555.
31. Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
32. Davis, F. A.; Reddy, T. R.; Reddy, R. E. J. Org. Chem. 1992, 57, 6387.
33. For a review on the chemistry of sulfmimines, see Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
34. For recent reviews on the chemistry of imines, see (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 12, p 355. (b) Kleinman, E. F. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4, p 893. Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
35. For recent reviews on the chemistry of imines, see (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 12, p 355. (b) Kleinman, E. F. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4, p 893. Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
36. For recent reviews on the chemistry of imines, see (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 12, p 355. (b) Kleinman, E. F. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4, p 893. Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
37. For recent reviews on the chemistry of imines, see (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 12, p 355. (b) Kleinman, E. F. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4, p 893. Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
38. Anet, F. A. L.; Trepka, R. D.; Cram, D. J. J. Am. Chem. Soc. 1967, 89, 357. Raban, M.; Kost, D. J. Am. Chem. Soc. 1972, 94, 3234.
39. Anet, F. A. L.; Trepka, R. D.; Cram, D. J. J. Am. Chem. Soc. 1967, 89, 357. Raban, M.; Kost, D. J. Am. Chem. Soc. 1972, 94, 3234.
40. Methyl N-(phenylsulfinyl)-2-aziridinecarboxylate is reported to prefer the trans-configuration. Chervin, I. I.; Fomichev, A. A.; Moskalenko, A. S.; Zaichenko, N. L. Aliev, A. E.; Prosyanik, A. V.; Voznesenskii, V. N.; Kostyanovskii, R. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 1110. Chem. Abstr. 1989, 110, 56755g.
41. Methyl N-(phenylsulfinyl)-2-aziridinecarboxylate is reported to prefer the trans-configuration. Chervin, I. I.; Fomichev, A. A.; Moskalenko, A. S.; Zaichenko, N. L. Aliev, A. E.; Prosyanik, A. V.; Voznesenskii, V. N.; Kostyanovskii, R. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 1110. Chem. Abstr. 1989, 110, 56755g.
42. The coupling constants for cis- and trans-2-(methoxycarbonyl)-3-phenylaziridines are 6.5 and 2.3 Hz, respectively. Ploux, O.; Caruso, M.; Chassaing, G.; Marquet, A. J. Org. Chem. 1988, 53, 3154.
43. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Andersopn, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
44. Thijs, L.; Porskamp, J. J. M.; van Loon, A. A. W. M.; Derks, M. P. W.; Feenstra, R. W.; Legters, J.; Zwanenburg, B. Tetrahedron 1990, 46, 2611.
45. Dharanipragada, R.; VanHulle, K.; Bannister, A.; Bear, S.; Kennedy, L.; Hruby, V. J. Tetrahedron 1992, 48, 4733.
46. Cainelli, G.; Panunzio, M. Tetrahedron Lett. 1991, 32, 121.
47. (a) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
48. (b) Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650.
49. (c) Oare, D. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 157.
50. Legters, J.; Willems, J. G. H.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 59.
51. Gentilucci, L.; Grijzen, Y.; Thija, L.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 4665.