Direct asymmetric aminoxylation reaction catalyzed by a binaphthyl-based chiral amino sulfonamide with high catalytic performance

Tetrahedron Letters

Volumn 49, Issue 37, 2008, Pages 5369-5371

  Kano, Taichi ^a   Yamamoto, Akihiro ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aminoxylation; Organocatalysis

Indexed keywords

AMINO SULFONAMIDE; BINAPHTHYL; NAPHTHALENE; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY;

EID: 48149090201     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.093     Document Type: Article

References (36)

1. For reviews, see:. Adam W., and Krebs O. Chem. Rev. 103 (2003) 4131
2. Merino P., and Tejero T. Angew. Chem., Int. Ed. 43 (2004) 2995
3. Janey J.M. Angew. Chem., Int. Ed. 44 (2005) 4292
4. Yamamoto H., and Momiyama N. Chem. Commun. (2005) 3514
5. Yamamoto Y., and Yamamoto H. Eur. J. Org. Chem. (2006) 2031
6. Yamamoto H., and Kawasaki M. Bull. Chem. Soc. Jpn. 80 (2007) 595
7. Momiyama N., and Yamamoto H. J. Am. Chem. Soc. 125 (2003) 6038
8. Representative papers:. Zhong G. Angew. Chem., Int. Ed. 42 (2003) 4247
9. Brown S.P., Brochu M.P., Sinz C.J., and MacMillan D.W.C. J. Am. Chem. Soc. 125 (2003) 10808
10. Hayashi Y., Yamaguchi J., Hibino K., and Shoji M. Tetrahedron Lett. 44 (2003) 8293
11. Bøgevig A., Sundén H., and Córdova A. Angew. Chem., Int. Ed. 43 (2004) 1109
12. Hayashi Y., Yamaguchi J., Sumiya T., and Shoji M. Angew. Chem., Int. Ed. 43 (2004) 1112
13. Yamamoto Y., Momiyama N., and Yamamoto H. J. Am. Chem. Soc. 126 (2004) 5962
14. Momiyama N., Torii H., Saito S., and Yamamoto H. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5374
15. Wang W., Wang J., Li H., and Liao L. Tetrahedron Lett. 45 (2004) 7235
16. Ramachary D.B., and Barbas III C.F. Org. Lett. 7 (2005) 1577
17. Kumarn S., Shaw D.M., Longbottom D.A., and Ley S.V. Org. Lett. 7 (2005) 4189
18. Huang K., Huang Z.-Z., and Li X.-L. J. Org. Chem. 71 (2006) 8320
19. Font D., Bastero A., Sayalero S., Jimeno C., and Pericàs M.A. Org. Lett. 9 (2007) 1943
20. Momiyama N., and Yamamoto H. J. Am. Chem. Soc. 127 (2005) 1080
21. Momiyama N., Yamamoto Y., and Yamamoto H. J. Am. Chem. Soc. 129 (2007) 1190
22. Momiyama N., and Yamamoto H. J. Am. Chem. Soc. 126 (2004) 5360
23. Guo H.-M., Cheng L., Cun L.-F., Gong L.-Z., Mi A.-Q., and Jiang Y.-Z. Chem. Commun. (2006) 429
24. Kano T., Ueda M., Takai J., and Maruoka K. J. Am. Chem. Soc. 128 (2006) 6046
25. Kim S.-G., and Park T.-H. Tetrahedron Lett. 47 (2006) 9067
26. Palomo C., Vera S., Velilla I., Mielgo A., and Gómez-Bengoa E. Angew. Chem., Int. Ed. 46 (2007) 8054
27. López-Cantarero C.J., Cid M.B., Poulsen T.B., Bella M., García Ruano J.L., and Jørgensen K.A. J. Org. Chem. 72 (2007) 7062
28. Yamamoto Y., and Yamamoto H. J. Am. Chem. Soc. 126 (2004) 4128
29. Yamamoto Y., and Yamamoto H. Angew. Chem., Int. Ed. 44 (2005) 7082
30. Jana C.K., and Studer A. Angew. Chem., Int. Ed. 46 (2007) 6542
31. Kano T., Yamamoto A., Mii H., Takai J., Shirakawa S., and Maruoka K. Chem. Lett. 37 (2008) 250
32. Kano T., Takai J., Tokuda O., and Maruoka K. Angew. Chem., Int. Ed. 44 (2005) 3055
33. Kano T., Tokuda O., Takai J., and Maruoka K. Chem. Asian J. 1 (2006) 210
34. Kano T., Yamaguchi Y., Tokuda O., and Maruoka K. J. Am. Chem. Soc. 127 (2005) 16408
35. Kano T., Yamaguchi Y., Tanaka Y., and Maruoka K. Angew. Chem., Int. Ed. 46 (2007) 1738
36. 4 and concentrated. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate = 4:1) to afford the corresponding aminoxylation product (22 mg, 0.13 mmol, 86% yield, 98% ee).