Stereoselective aminobromination of alkylidenecyclopropanes with TsNH 2 and NBS as nitrogen and bromine sources: A simple access to γ-bromohomoallylic sulfonamides

Synthesis

Volumn , Issue 6, 2006, Pages 1016-1020

  Huang, Xian ^a,b   Fu, Wei Jun ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkylidenecyclopropanes; Aminobromination; Homoallylic sulfonamide; N bromosuccinimide; p toluenesulfonamide; Stereoselective

Indexed keywords

BROMINE; NITROGEN; STEREOCHEMISTRY;

ALKYLIDENECYCLOPROPANES; AMINOBROMINATION; HOMOALLYLIC SULFONAMIDE; N-BROMOSUCCINIMIDE; P-TOLUENESULFONAMIDE; STEREOSELECTIVE;

PARAFFINS;

ACRYLIC ACID METHYL ESTER; BENZYLIDENECYCLOPROPANE; BROMIDE; GAMMA BROMOHOMMOALLYLIC SULFONAMIDE DERIVATIVE; IDENECYCLOPROPANE DERIVATIVE; N BROMOSUCCINIMIDE; NITROGEN; PROPANE; SULFONAMIDE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; STEREOCHEMISTRY;

EID: 33645356187     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926350     Document Type: Article

References (40)

1. (a) Jones, A. D.; Knight, D. W. Chem. Commun. 1996, 915.
2. (b) Jones, A. D.; Knight, D. W.; Redfern, A. L. Tetrahedron Lett. 1999, 40, 3267.
3. (c) Jones, A. D.; Knight, D. W.; Hibbs, D. E. J. Chem. Soc., Perkin Trans. 1 2001, 1182.
4. (d) Haskins, C. M.; Knight, D. W. Chem. Commun. 2002, 2724.
5. (a) Mitsunobu, O. Synthesis 1981, 1.
6. (b) Mitsunobu, O. In Comprehensive Organic Synthesis, Vol. 6; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 65.
7. (c) Hughes, D. L. Org. React. 1992, 42, 335.
8. Neipp, C. E.; Humphrey, J. M.; Martin, S. F. J. Org. Chem. 2001, 66, 531.
9. Synthesis of MCPs: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
10. Recent reviews of MCPs: (a) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
11. (b) Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 2, 111.
12. (c) Yamago, S.; Nakamura, E. Org. React. 2002, 61, 1.
13. (d) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
14. (e) Yamago, S.; Takeichi, A.; Nakamura, E. Synthesis 1996, 1380.
15. (f) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77.
16. (g) Ohta, T.; Takaya, H. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Ed.; Pergamon: Oxford, 1991, 1185.
17. (a) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015.
18. (b) Lautens, M.; Ren, Y. J. Am. Chem. Soc. 1996, 118, 9597.
19. (c) Itazaki, M.; Nishihara, Y.; Osakada, K. J. Org. Chem. 2002, 67, 6889.
20. (d) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661.
21. (e) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2002, 67, 3445.
22. (f) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270.
23. (g) Shi, M.; Chen, Y.; Xu, B. Org. Lett. 2003, 5, 1225.
24. (h) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790.
25. (i) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Tveritinova, E. V.; Yu'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069.
26. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458.
27. (k) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
28. (a) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019.
29. (b) Shi, M.; Chen, Y. J. Org. Chem. 2004, 69, 426.
30. (a) Huang, X.; Zhou, H. W. Org. Lett. 2002, 4, 4419.
31. (b) Zhou, H. W.; Huang, X.; Chen, W. L. Synlett 2003, 2080.
32. (c) Huang, X.; Zhou, H. W.; Chen, W. L. J. Org. Chem. 2004, 69, 839.
33. Chen, W. L.; Huang, X.; Zhou, H. W. Synthesis 2004, 1573.
34. Thakur, V. V.; Talluri, S. K.; Sudalai, A. Org. Lett. 2003, 5, 861.
35. Kozhushkov, S.; Fiebig, T.; Galland, B.; Ruasse, M. F.; Xavier, P.; Apeloig, Y.; de Meijere, A. J. Org. Chem. 2002, 67, 4100.
36. Siriwardana, A. I.; Nakamura, I.; Yamamoto, Y. Tetrahedron Lett. 2003, 44, 985.
37. Shao, L. X.; Zhao, L. J.; Shi, M. Eur. J. Org. Chem. 2004, 4894.
38. (a) Brase, S.; Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 99.
39. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
40. (c) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.