Sulfonyl hydrazine as new functionality in organocatalysis: Camphorsulfonyl hydrazine catalyzed enantioselective Aza-Michael addition

Synthesis

Volumn , Issue 9, 2009, Pages 1573-1577

  Chen, Ling Yan ^a   He, Hao ^a   Pei, Bao Jian ^a   Chan, Wing Hong ^a   Lee, Albert W M ^a  

^a HONG KONG BAPTIST UNIVERSITY   (Hong Kong)

Author keywords

, unsaturated aldehyde; Aza Michael addition; Camphorsulfonyl hydrazine; Organocatalysis; Sulfonyl hydrazine

Indexed keywords

AZA-MICHAEL ADDITION; CAMPHORSULFONYL HYDRAZINE; ENANTIOSELECTIVE; LEWIS BASE; ORGANOCATALYSIS; ORGANOCATALYSTS; SULFONYL HYDRAZINE; UNSATURATED ALDEHYDES;

ADDITION REACTIONS; ALDEHYDES; CATALYSIS; ENANTIOSELECTIVITY; RATE CONSTANTS; REACTION KINETICS;

HYDRAZINE;

CAMPHOR SULFONYL HYDRAZINE; HYDRAZINE DERIVATIVE; LEWIS BASE; SULFONYL HYDRAZINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; SUBSTITUTION REACTION;

EID: 67650079016     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216639     Document Type: Article

References (49)

1. (a) List, B.; Lerner, R. A.; Barbas, C. F. III J. Am. Chem. Soc. 2000, 122, 2395.
2. (b) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
3. (c) List, B. Chem. Commun. 2006, 819.
4. (d) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471.
5. (e) Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416.
6. (f) Taylor, M. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2006, 45, 1520.
7. (g) Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713.
8. (h) Akiyama, T. Chem. Rev. 2007, 107, 5744.
9. (i) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999.
10. (j) Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518.
11. (k) Shirakawa, S.; Yamamoto, K.; Kitamura, M.; Ooi, T.; Maruoka, K. Angew. Chem. Int. Ed. 2005, 44, 625.
12. (l) Ooi, T.; Maruoka, K. Angew. Chem. Int. Ed. 2007, 46, 4222.
13. (m) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656.
14. (n) Merino, P.; Marques-Lopez, E.; Herrera, R. P. Adv. Synth. Catal. 2008, 350, 1195.
15. (o) Dondoni, A.; Massi, A. Angew. Chem. Int. Ed. 2008, 47, 2.
16. A similar term 'organic catalysis' had first appeared in the German literature: Langenbeck, W. Fortschr. Chem. Forsch. 1966, 6, 301.
17. List, B. Chem. Rev. 2007, 107, 5413.
18. For an excellent review on iminium ion activation, see: (a) Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 39, 79.
19. (b) Ref. 1e.
20. For selected examples, see: (a) Brandes, S.; Niess, B.; Bella, M.; Prieto, A.; Overgaard, J.; Jorgensen, K. A. Chem. Eur. J. 2006, 12, 6039.
21. (b) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jorgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790.
22. (c) Bertelsen, S.; Halland, N.; Bachmann, S.; Marigo, M.; Braunton, A.; Jorgensen, K. A. Chem.Commun. 2005, 4821.
23. (d) Wang, J.; Li, H.; Mei, Y.; Lou, B.; Xu, D.; Xie, D.; Gou, H.; Wang, W. J. Org. Chem. 2005, 70, 5678.
24. (e) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167.
25. (f) Ibrahem, I.; Cordova, A. Chem. Commun. 2006, 1760.
26. (g) Yua, X.-H.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037.
27. (h) Ye, L.-W.; Zhou, J.; Shao, Z.-H. J. Mol. Catal. A: Chem. 2008, 285, 1.
28. Sander, E. G.; Jencks, W. P. J. Am. Chem. Soc. 1968, 90, 6154.
29. (a) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
30. (b) Cavill, J. L.; Elliott, R. L.; Evans, G.; Jones, I. L.; Platts, J. A.; Ruda, A. M.; Tomkinson, N. C. O. Tetrahedron 2006, 62, 410.
31. (c) Cavill, J. L.; Peters, J.-U.; Tomkinson, N. C. O. Chem. Commun. 2003, 728.
32. (d) Dirksen, A.; Hackeng, T. M.; Dawson, P. E. Angew. Chem. Int. Ed. 2006, 45, 7581.
33. (a) Lemay, M.; Ogilvie, W. W. Org. Lett. 2005, 7, 4141.
34. (b) Lemay, M.; Ogilvie, W. W. J. Org. Chem. 2006, 71, 4663.
35. (c) Lemay, M.; Aumand, L.; Ogilvie, W. W. Adv. Synth. Catal. 2007, 349, 441.
36. He, H.; Pei, B.-J.; Chou, H. H.; Tian, T.; Chan, W. H.; Lee, A. W. M. Org. Lett. 2008, 10, 2421.
37. Langlois, Y.; Petit, A.; Rémy, P.; Scherrmann, M. C.; Kouklovsky, C. Tetrahedron Lett. 2008, 49, 5576.
38. (a) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
39. (b) Nájera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584.
40. For reviews of the Michael addition catalyzed by metallic complexes, see: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
41. (b) Krause, N.; Hoffmann-Roder Synthesis 2001, 171.
42. (c) Christoffers, J.; Koripelly, G.; Rosiak, A. Synthesis 2007, 1279.
43. (d) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
44. (a) Marigo, M.; Jorgensen, K. A. Chem. Commmun. 2006, 2001.
45. (b) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 18, 1701.
46. (c) Almasi, D.; Alonso, D. A.; Najera, C. Tetrahedron: Asymmetry 2007, 18, 299.
47. (d) Vicario, J. L.; Badia, D.; Carrillo, L. Synthesis 2007, 2065.
48. Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328.
49. Vesely, J.; Ibrahem, I.; Rios, R.; Zhao, G.-L.; Xu, Y.-M.; Còrdova, A. Tetrahedron Lett. 2007, 48, 2193.