The synthesis of enantiomerically pure disubstituted aziridines and N- alkoxy aziridines

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 787-790

  Hanessian, Stephen ^a   Cantin, Louis David ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034607006     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02211-X     Document Type: Article

References (37)

1. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599; Osborn, H. M.; Sweeny, J. Tetrahedron: Asymmetry 1997, 8, 1693; Padwa, A.; Woodhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p. 47.
2. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599; Osborn, H. M.; Sweeny, J. Tetrahedron: Asymmetry 1997, 8, 1693; Padwa, A.; Woodhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p. 47.
3. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599; Osborn, H. M.; Sweeny, J. Tetrahedron: Asymmetry 1997, 8, 1693; Padwa, A.; Woodhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, p. 47.
4. See, for example: Schirmeister, T. J. Med. Chem. 1999, 42, 560; Kasai, M.; Kono, M. Synlett 1992, 778; Gerhart, R; Higgins, W.; Tardif, C.; Ducep, J.-B. J. Med. Chem. 1990, 33, 2157.
5. See, for example: Schirmeister, T. J. Med. Chem. 1999, 42, 560; Kasai, M.; Kono, M. Synlett 1992, 778; Gerhart, R; Higgins, W.; Tardif, C.; Ducep, J.-B. J. Med. Chem. 1990, 33, 2157.
6. See, for example: Schirmeister, T. J. Med. Chem. 1999, 42, 560; Kasai, M.; Kono, M. Synlett 1992, 778; Gerhart, R; Higgins, W.; Tardif, C.; Ducep, J.-B. J. Med. Chem. 1990, 33, 2157.
7. Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517.
8. For recent examples, see: Bergmeier, S. C.; Seth, P. P. J. Org. Chem. 1999, 64, 3237; Wipf, P.; Venkatraman, S. Synlett 1997, 1; Hudlickly, T.; Tian, X.; Königsberger, K.; Mauryan, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. See also Ref. 1.
9. For recent examples, see: Bergmeier, S. C.; Seth, P. P. J. Org. Chem. 1999, 64, 3237; Wipf, P.; Venkatraman, S. Synlett 1997, 1; Hudlickly, T.; Tian, X.; Königsberger, K.; Mauryan, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. See also Ref. 1.
10. For recent examples, see: Bergmeier, S. C.; Seth, P. P. J. Org. Chem. 1999, 64, 3237; Wipf, P.; Venkatraman, S. Synlett 1997, 1; Hudlickly, T.; Tian, X.; Königsberger, K.; Mauryan, R.; Rouden, J.; Fan, B. J. Am. Chem. Soc. 1996, 118, 10752. See also Ref. 1.
11. Toda, A.; Aoyama, H.; Mimura, N.; Ohno, H.; Fujii, N.; Ibuka, T. J. Org. Chem. 1998, 63, 7053; Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784; Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735; Dauban, P.; Dubois, L.; Tran Huu Dau, M. E.; Dodd, R. J. Org. Chem. 1995, 60, 2035.
12. Toda, A.; Aoyama, H.; Mimura, N.; Ohno, H.; Fujii, N.; Ibuka, T. J. Org. Chem. 1998, 63, 7053; Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784; Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735; Dauban, P.; Dubois, L.; Tran Huu Dau, M. E.; Dodd, R. J. Org. Chem. 1995, 60, 2035.
13. Toda, A.; Aoyama, H.; Mimura, N.; Ohno, H.; Fujii, N.; Ibuka, T. J. Org. Chem. 1998, 63, 7053; Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784; Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735; Dauban, P.; Dubois, L.; Tran Huu Dau, M. E.; Dodd, R. J. Org. Chem. 1995, 60, 2035.
14. Toda, A.; Aoyama, H.; Mimura, N.; Ohno, H.; Fujii, N.; Ibuka, T. J. Org. Chem. 1998, 63, 7053; Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784; Zwanenburg, B.; Thijs, L. Pure Appl. Chem. 1996, 68, 735; Dauban, P.; Dubois, L.; Tran Huu Dau, M. E.; Dodd, R. J. Org. Chem. 1995, 60, 2035.
15. Backer, H. J. Rec. Trav. Chim. Pays-Bas 1950, 69, 1223; for intramolecular aziridination to N-methoxy aziridines, see: Wright, D. L.; McMills, M. C. Org. Lett. 1999, 1, 667.
16. Backer, H. J. Rec. Trav. Chim. Pays-Bas 1950, 69, 1223; for intramolecular aziridination to N-methoxy aziridines, see: Wright, D. L.; McMills, M. C. Org. Lett. 1999, 1, 667.
17. Perrocheau, J.; Carrié, R.; Fleury, J.-P. Can. J. Chem. 1994, 72, 2458.
18. Vedejs, E.; Sano, H. Tetrahedron Lett. 1992, 33, 3261; Rudchenko, V. F.; Ignatov, S. M.; Kostyanovsky, G. J. Chem. Soc., Chem. Commun. 1990, 261.
19. Vedejs, E.; Sano, H. Tetrahedron Lett. 1992, 33, 3261; Rudchenko, V. F.; Ignatov, S. M.; Kostyanovsky, G. J. Chem. Soc., Chem. Commun. 1990, 261.
20. Bosies, E.; Kampe, W.; Thiel, M.; Bicker, U.; Boerner, D. US 4,517,183, 1985.
21. Rudchenko, V. F.; D'Yachenko, O. A.; Zolotoi, A. B.; Atovmyan, L. V.; Chervin, I. I.; Kostyanovsky, R. G. Tetrahedron 1982, 38, 961.
22. Prosnyanik, A. V.; Mishchenko, A. I.; Zaichenko, N. L.; Shustov, G. V.; Nelov, P. N.; Kostyanovsky, R. G. Bull. Acad. Sci. USSR. Div. Chem. Sci. (Engl. Trans.) 1984, 33, 546.
23. Prosnyanik, A. V.; Bondarenko, S. V.; Markov, V. I.; Chervin, I. I.; Isobaev, M. D.; Kushch, S. D.; Kostyanovsky, R. G. Chem. Heterocycl. Compd. (Engl. Transl.) 1980, 16, 154; Pierre, J.-L.; Baret, P.; Arnaud, P. Bull. Soc. Chem. Fr. 1971, 3619; Brois, S. J. J. Am. Chem. Soc. 1970, 92, 1079.
24. Prosnyanik, A. V.; Bondarenko, S. V.; Markov, V. I.; Chervin, I. I.; Isobaev, M. D.; Kushch, S. D.; Kostyanovsky, R. G. Chem. Heterocycl. Compd. (Engl. Transl.) 1980, 16, 154; Pierre, J.-L.; Baret, P.; Arnaud, P. Bull. Soc. Chem. Fr. 1971, 3619; Brois, S. J. J. Am. Chem. Soc. 1970, 92, 1079.
25. Prosnyanik, A. V.; Bondarenko, S. V.; Markov, V. I.; Chervin, I. I.; Isobaev, M. D.; Kushch, S. D.; Kostyanovsky, R. G. Chem. Heterocycl. Compd. (Engl. Transl.) 1980, 16, 154; Pierre, J.-L.; Baret, P.; Arnaud, P. Bull. Soc. Chem. Fr. 1971, 3619; Brois, S. J. J. Am. Chem. Soc. 1970, 92, 1079.
26. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393.
27. Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J.-B. Chem. Comm. 1996, 2631; Florio, S.; Troisi, L.; Capriati, V. J. Org. Chem. 1995, 60, 2279.
28. Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J.-B. Chem. Comm. 1996, 2631; Florio, S.; Troisi, L.; Capriati, V. J. Org. Chem. 1995, 60, 2279.
29. Bunz, U.; Herpich, W.; Podlech, J.; Polborn, K.; Pratzel, A.; Stephenson, D. S.; Szeimies, G. J. Am. Chem. Soc. 1994, 116, 7637; Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891; Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 162.
30. Bunz, U.; Herpich, W.; Podlech, J.; Polborn, K.; Pratzel, A.; Stephenson, D. S.; Szeimies, G. J. Am. Chem. Soc. 1994, 116, 7637; Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891; Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 162.
31. Bunz, U.; Herpich, W.; Podlech, J.; Polborn, K.; Pratzel, A.; Stephenson, D. S.; Szeimies, G. J. Am. Chem. Soc. 1994, 116, 7637; Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891; Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 162.
32. Ambrosi, H.-D.; Duczek, W.; Ramm, M.; Jähnisch, K. Tetrahedron Lett. 1994, 35, 7613.
33. For reviews and leading references, see: Romine, J. L.; Org. Prep. Proc. Int. 1996, 251; Sandler, S. R.; Karo, W. In Organic Functional Group Preparations; Wasserman, H. H., Ed.; Academic Press: San Diego, 1989; Vol. 3, pp. 482; Ottenheijm, H. C. J.; Heirscheid, J. D. M. Chem. Rev. 1986, 86, 697.
34. For reviews and leading references, see: Romine, J. L.; Org. Prep. Proc. Int. 1996, 251; Sandler, S. R.; Karo, W. In Organic Functional Group Preparations; Wasserman, H. H., Ed.; Academic Press: San Diego, 1989; Vol. 3, pp. 482; Ottenheijm, H. C. J.; Heirscheid, J. D. M. Chem. Rev. 1986, 86, 697.
35. For reviews and leading references, see: Romine, J. L.; Org. Prep. Proc. Int. 1996, 251; Sandler, S. R.; Karo, W. In Organic Functional Group Preparations; Wasserman, H. H., Ed.; Academic Press: San Diego, 1989; Vol. 3, pp. 482; Ottenheijm, H. C. J.; Heirscheid, J. D. M. Chem. Rev. 1986, 86, 697.
36. Jahngen Jr., E. G. E.; Rossomando, E. F. Syn. Commun. 1982, 12, 601.
37. Hanessian, S.; Lu, P.-P., Sancéau, J.-Y.; Chemla, P.; Gohda, K.; Fonne-Pfister, R.; Prade, L.; Cowan-Jacob, S. Angew. Chem., Int. Ed. 1999, 38, 3159.