Enantioselective intramolecular C-H amidation of sulfamate esters catalyzed by chiral dirhodium(II) carboxylates

Heterocycles

Volumn 69, Issue 1, 2006, Pages 527-537

  Yamawaki, Minoru ^a   Kitagaki, Shinji ^a   Anada, Masahiro ^a   Hashimoto, Shunichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947249423     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-s(o)49     Document Type: Article

References (46)

1. For recent reviews on intramolecular C-H amidation reactions, see:. Müller P. In: Doyle M.P. (Ed) (1997), JAI Press, Greenwich 113
2. Dauban P., and Dodd R.H. Synlett (2003) 1571
3. Chapter 12. Doyle M.P. Reactive Intermediate Chemistry. In: Moss R.A., Platz M.S., and Jones Jr. M. (Eds) (2004), John Wiley & Sons, Hoboken
4. Müller P., and Fruit C. Chem. Rev. 103 (2003) 2905
5. Davies H.M.L., and Long M.S. Angew. Chem. Int. Ed. 44 (2005) 3518
6. Chapter 17. Espino C.G., and Du Bois J. Modern Rhodium-Catalyzed Organic Reactions. In: Evans P.A. (Ed) (2005), Wiley-VCH, Weinheim
7. Breslow R., and Gellman S.H. J. Am. Chem. Soc. 105 (1983) 6728
8. Espino C.G., and Du Bois J. Angew. Chem. Int. Ed. 40 (2001) 598
9. Espino C.G., Wehn P.M., Chow J., and Du Bois J. J. Am. Chem. Soc. 123 (2001) 6935
10. Wehn P.M., Lee J., and Du Bois J. Org. Lett. 5 (2003) 4823
11. Espino C.G., Fiori K.W., Kim M., and Du Bois J. J. Am. Chem. Soc. 126 (2004) 15378
12. Wehn P.M., and Du Bois J. Org. Lett. 7 (2005) 4685
13. For selected examples of natural product synthesis via intramolecular C-H amidation with in situ generated iminoiodinanes, see
14. Wehn P.M., and Du Bois J. J. Am. Chem. Soc. 124 (2002) 12950
15. Hinman A., and Du Bois J. J. Am. Chem. Soc. 125 (2003) 11510
16. Parker K.A., and Chang W. Org. Lett. 7 (2005) 1785
17. Toumieux S., Compain P., and Martin O.R. Tetrahedron Lett. 46 (2005) 4731
18. Yakura T., Yoshimoto Y., Ishida C., and Mabuchi S. Synlett (2006) 930
19. For selected examples of transition metal-catalyzed nitrene transfer reactions with in situ generated iminoiodinanes, see:. Au S.-M., Huang J.-S., Che C.-M., and Yu W.-Y. J. Org. Chem. 65 (2000) 7858
20. Yu X.-Q., Huang J.-S., Zhou X.-G., and Che C.-M. Org. Lett. 2 (2000) 2233
21. Dauban P., and Dodd R.H. Org. Lett. 2 (2000) 2327
22. Dauban P., Sanière L., Tarrade A., and Dodd R.H. J. Am. Chem. Soc. 123 (2001) 7707
23. Liang J.-L., Yuan S.-X., Huang J.-S., Yu W.-Y., and Che C.-M. Angew. Chem. Int. Ed. 41 (2002) 3465
24. Liang J.-L., Yuan S.-X., Huang J.-S., and Che C.-M. J. Org. Chem. 69 (2004) 3610
25. Zhang J., Chan P.W.H., and Che C.-M. Tetrahedron Lett. 46 (2005) 5403
26. Cui Y., and He C. Angew. Chem. Int. Ed. 43 (2004) 4210
27. Fruit C., and Müller P. Tetrahedron: Asymmetry 15 (2004) 1019
28. Fruit C., and Müller P. Helv. Chim. Acta 87 (2004) 1607
29. Yamawaki M., Tsutsui H., Kitagaki S., Anada M., and Hashimoto S. Tetrahedron Lett. 43 (2002) 9561
30. Watanabe N., Ogawa T., Ohtake Y., Ikegami S., and Hashimoto S. Synlett (1996) 85
31. Anada M., and Hashimoto S. Tetrahedron Lett. 39 (1998) 79
32. Anada M., and Hashimoto S. Tetrahedron Lett. 39 (1998) 9063
33. Kitagaki S., Yasugahira M., Anada M., Nakajima M., and Hashimoto S. Tetrahedron Lett. 41 (2000) 5931
34. Takahashi T., Tsutsui H., Tamura M., Kitagaki S., Nakajima M., and Hashimoto S. Chem. Commun. (2001) 1604
35. Kitagaki S., Yanamoto Y., Tsutsui H., Anada M., Nakajima M., and Hashimoto S. Tetrahedron Lett. 42 (2001) 6361
36. Tsutsui H., Matsuura M., Makino K., Nakamura S., Nakajima M., Kitagaki S., and Hashimoto S. Isr. J. Chem. 41 (2001) 283
37. Saito H., Oishi H., Kitagaki S., Nakamura S., Anada M., and Hashimoto S. Org. Lett. 4 (2002) 3887
38. Minami K., Saito H., Tsutsui H., Nambu H., Anada M., and Hashimoto S. Adv. Synth. Catal. 347 (2005) 1483
39. 4, see:. Tsutsui H., Abe T., Nakamura S., Anada M., and Hashimoto S. Chem. Pharm. Bull. 53 (2005) 1366
40. Alker D., Doyle K.J., Harwood L.M., and McGregor A. Tetrahedron: Asymmetry 1 (1990) 877
41. The use of ethyl acetate required 20 h for completion of the reaction, giving 6a in 87% yield with 15% ee.
42. 2, 40 °C, 3.5 h] provides 6a with 18% ee, see Ref. 8b.
43. Tsutsui H., Yamaguchi Y., Kitagaki S., Nakamura S., Anada M., and Hashimoto S. Tetrahedron: Asymmetry 14 (2003) 817
44. Appel R., and Berger G. Chem. Ber. 91 (1958) 1339
45. Okada M., Iwashita S., and Koizumi N. Tetrahedron Lett. 41 (2000) 7047
46. Winum J.-Y., Vullo D., Casini A., Montero J.-L., Scozzafava A., and Supuran C.T. J. Med. Chem. 46 (2003) 5471