Metal-free intramolecular aziridination of alkenes using hypervalent iodine based sulfonyliminoiodanes

Organic Letters

Volumn 12, Issue 2, 2010, Pages 364-366

  Moriarty, Robert M ^a   Tyagi, Sachin ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; IODINE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKENES; AZIRIDINES; CYCLIZATION; IODINE; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 74949138970     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9026655     Document Type: Article

References (44)

1. For reviews, see: (a) Müller, P. Acc. Chem. Res. 2004, 37, 243.
2. (b) Doyle. M. P.; Forbes. D. C. Chem. Rev. 1998, 98, 911.
3. (c)Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
4. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
5. (e) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893.
6. (a) Müller. P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
7. (b) Guthikonda, K.; When, P. M.: Caliando, B. J.; DuBois, J. Tetrahedron 2006, 62, 11331.
8. (c) Dauban, P.: Dodd, R. H. Syn. Lett. 2003, 11, 1571.
9. (d) First example of Cu(I) or Cu(II) catalysis: Evans. D. A.; Faul, M. M.: Bilodeau. M. T. J. Org. Chem. 1991, 56, 6744.
10. (e) Evans, D. A.; Bilodeau. M. T.: Faul, M. M. J. Am. Chem. Soc. 1994, 116, 2742.
11. (f) Rovis, T.; Evans, D. A. Prog. Inorg. Chem. 2001, 50, 1.
12. (g) Yamada. Y.; Yamamoto. T.; Okawara, M. Chem. Lett. 1975, 361.
13. (h) Li, Z.: Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326. Use of Rh(II):
14. (i) Liang, J.-L.; Yuan, S.-X.: Chan. P. W. H.: Che, C.-M. Org. Lett. 2002, 4, 4507.
15. For the first example of this intramolecular thermal nonmetal process, see: (a) Moriarty, R. M.; Prakash, O.: Vaid, R. K.; Zhao, L. J. Am. Chem Soc. 1989, 111, 6443.
16. Erratum J. Am. Chem. Soc. 1990, 112, 1297.
17. (b) Gallos. J. K.; Koftis, T. V.; Massen, Z. S.; Dellios. C. C.; Mourtzinos. I. T.; Coutouli-Argyropoulou, E.; Koumbis. A. E. Tetrahedron 2002, 58, 8043.
18. For a comparison of the intramolecular cyclopropanation using Cu(I). Rh(II). and nonmetal, see: (c) Müller, P.; Bolea, C. Synlett 2000, 826.
19. (d) Müller, P.; Bolea. C. Helv. Chim. Acta 2001, 84. 1093.
20. A recent example of this effort is the achievement of a copper-free Sonogashira coupling: (a) Appukkuttan, P.; Dehaen, W.; Van der Eycken. E. Eur. J. Org. Chem. 2003, 4713.
21. (b) Leadbeater. N. E.; Marco. M.; Tominack, B. J. Org. Lett. 2003, 5, 3919.
22. (c) Luque, R.; Macquarrie, D. J. Org. Bio. Chem. 2009, 7, 1627.
23. For toxicity of copper, see: (d) Flemming, C. A.; Trevors, J. T. Water Air Soil Poll. 1989, 44, 143.
24. (e) Use of organohypervalent iodine reagents as substitutes for Pb(IV), T1(III), and Hg(II) has been pursued (ref le). Use of the Dess-Martin reagent, IBX. and PhIO as oxidants in place of Cr(VI) (ref lc) and use of IBX as a substitute for Se(IV) for conjugated carbonyl compound synthesis are relevant advances.
25. (f) Nicolaou. K. C.; Zhong, Y.-L.; Baran. P. S. J. Am. Chem. Soc. 2000, 122, 75960.
26. (g) A striking example of metal replacement is the use of fullerene inplace of noble metals in catalytic hydrogenation: Li, B.; Xu, Z. J. Am. Chem. Soc. 2009, 131, 16380.
27. (a) Evans. D. A.; Bilodeau, M. T.: Faul, M. M. J. Am. Chem. Soc. 1994, 116, 2742.
28. (b) Li. Z.: Cotiser, K. R.: Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
29. An example of the Rh(II) and nonmetal intramolecular cyclization of a cycloalkenyl carbamate with I(III) has been reported: Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137.
30. 7 can be accomplished via thermal or photochemical generation of nitrenes from azides just as cyclopropanation can be effected by thermal or photochemical decomposition of diazocompounds. For other metal-free intermolecular alkene aziridination processes, see: (a) Li, J.; Liang, J.-L.; Chan, P. W. H.; Che, C.-M. tetrahedron Lett. 2004, 45, 2685.
31. (b) Li, J.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2005, 7, 5801.
32. (c) Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844.
33. (d) Minakata, S.; Morino, Y.; Oderaotoshi, Y.; Komatsu, M. J. Chem. Soc., Chem. Commun. 2006, 3337.
34. (e) Minakata, S. Acc. Chem. Res. 2009, 42, 1172.
35. (a) Dauban, P.; Dodd, R. H. Org. Lett. 2000, 2, 2327.
36. (b) Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507.
37. White, R. E. Inorg. Chem. 1987, 26, 3916.
38. For an example of (1→5→6→4), see: Cochran, B. M.; Michael, F. E. Org. Lett. 2008, 10, 5039.
39. Bressan, M.; Morvillo, A. Inorg. Chem. 1989, 28, 950.
40. Ochiai, M.; Kaneaki, T.; Tada, N.; Miyamoto, K.; Chuman, H.; Shiro, M.; Hayashi, S.; Nakanishi, W. J. Am. Chem Soc. 2007, 129, 12938.
41. For an example of stable four-membered tricoordinated iodine(III) heterocycle, see: Kawashima, T.; Hoshiba, K.; Kano, N. J. Am. Chem. Soc. 2001, 123, 1507.
42. Sodergren, M. J.; Alonso, D. A.; Andersson, P. G. Tetrahedron: Asymmetry 1997, 8, 3563.
43. Moriarty, R. M.; Tyagi, S.; Ivanov, D.; Constantinescu, M. J. Am. Chem. Soc. 2008, 130, 7564.
44. Wehn, P. M.; Du Bois, J. Angew. Chem., Int. Ed. 2009, 48, 3802.