Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening

Organic Letters

Volumn 6, Issue 22, 2004, Pages 4109-4112

  Han, Hoon ^a   Bae, Imhyuck ^a   Eun, Jeong Yoo ^a   Lee, Junseong ^a   Do, Youngkyu ^a   Chang, Sukbok ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHELATION; RING OPENING; SUBSTITUTION REACTION;

EID: 8744317132     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0481784     Document Type: Article

References (30)

1. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
2. (a) Jun, C.-H.; Hong, J.-B.; Lee, D.-Y. Synlett 1999, 1.
3. (b) Itami, K.; Mitsudo, K.; Nokami, T.; Kamei, T.; Koike, T.; Yoshida, J. J. Organomet. Chem. 2002, 653, 105.
4. (c) Kakiuchi, F.; Chanati, N. Adv. Synth. Catal. 2003, 345, 1077.
5. For recent reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905. (c) Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586.
6. For recent reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905. (c) Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586.
7. For recent reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905. (c) Dauban, P.; Dodd, R. H. Synlett 2003, 1571-1586.
8. For selected examples of Cu-catalyzed aziridination, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744. (b) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326. (c) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
9. For selected examples of Cu-catalyzed aziridination, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744. (b) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326. (c) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
10. For selected examples of Cu-catalyzed aziridination, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744. (b) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326. (c) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
11. For some examples of aziridination methods catalyzed by other metals than copper: (a) Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C. M. J. Am. Chem. Soc. 1999, 121, 9120. (b) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672. (c) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507. (d) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
12. For some examples of aziridination methods catalyzed by other metals than copper: (a) Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C. M. J. Am. Chem. Soc. 1999, 121, 9120. (b) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672. (c) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507. (d) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
13. For some examples of aziridination methods catalyzed by other metals than copper: (a) Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C. M. J. Am. Chem. Soc. 1999, 121, 9120. (b) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672. (c) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507. (d) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
14. For some examples of aziridination methods catalyzed by other metals than copper: (a) Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C. M. J. Am. Chem. Soc. 1999, 121, 9120. (b) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672. (c) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507. (d) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
15. (a) Södergren, M. J.; Alonso, D. A.; Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1997, 38, 6897.
16. (b) Dauban, P.; Dodd, R. H. J. Org. Chem. 1999, 64, 5304.
17. Recent reports from this laboratory regarding on the chelation approach: (a) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (b) Ko, S.; Lee, C.; Choi, M.-G.; Na, Y.; Chang, S. J. Org. Chem. 2003, 68, 1607. (c) Ko, S.; Han, H.; Chang, S. Org. Lett. 2003, 5, 2687. (d) Na, Y.; Ko, S.; Hwang, L. K. Tetrahedron Lett. 2003, 44, 4475.
18. Recent reports from this laboratory regarding on the chelation approach: (a) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (b) Ko, S.; Lee, C.; Choi, M.-G.; Na, Y.; Chang, S. J. Org. Chem. 2003, 68, 1607. (c) Ko, S.; Han, H.; Chang, S. Org. Lett. 2003, 5, 2687. (d) Na, Y.; Ko, S.; Hwang, L. K. Tetrahedron Lett. 2003, 44, 4475.
19. Recent reports from this laboratory regarding on the chelation approach: (a) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (b) Ko, S.; Lee, C.; Choi, M.-G.; Na, Y.; Chang, S. J. Org. Chem. 2003, 68, 1607. (c) Ko, S.; Han, H.; Chang, S. Org. Lett. 2003, 5, 2687. (d) Na, Y.; Ko, S.; Hwang, L. K. Tetrahedron Lett. 2003, 44, 4475.
20. Recent reports from this laboratory regarding on the chelation approach: (a) Ko, S.; Na, Y.; Chang, S. J. Am. Chem. Soc. 2002, 124, 750. (b) Ko, S.; Lee, C.; Choi, M.-G.; Na, Y.; Chang, S. J. Org. Chem. 2003, 68, 1607. (c) Ko, S.; Han, H.; Chang, S. Org. Lett. 2003, 5, 2687. (d) Na, Y.; Ko, S.; Hwang, L. K. Tetrahedron Lett. 2003, 44, 4475.
21. Kwong, H.-L.; Liu, D.; Chan, K.-Y.; Lee, C.-S.; Huang, K.-H.; Che, C.-M. Tetrahedron Lett. 2004, 45, 3965.
22. For mechanistic studies in Cu-catalyzed aziridination, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742. (b) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889. (b) Brandt, P.; Södergren, M. J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013.
23. For mechanistic studies in Cu-catalyzed aziridination, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742. (b) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889. (b) Brandt, P.; Södergren, M. J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013.
24. For mechanistic studies in Cu-catalyzed aziridination, see: (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742. (b) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889. (b) Brandt, P.; Södergren, M. J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013.
25. For details, see the Supporting Information.
26. For a review, see: Hu, X. E. Tetrahedron 2004, 60, 2701.
27. Kozikowski, A. P.; Ishida, H.; Isobe, K. J. Org. Chem. 1979, 44, 2788.
28. Pak, C. S.; Lim, D. S. Synth. Commun. 2001, 31, 2209.
29. Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383 and references therein.
30. In fact, the desulfonylation from 3 and 5a/5b was incomplete and nonselective under the same conditions as for 4 and 6a/6b. For a relevant method of deprotection of N-tosyl group from aziridines, see: Alonso, D. A.; Andersson, P. G. J. Org. Chem. 1998, 63, 9455.