Mild Michael addition of glycine imines to aromatic nitroalkenes catalyzed by DBU with LiOTf as an additive

Synlett

Volumn , Issue 6, 2009, Pages 925-928

  Li, Wei ^a   Liu, Han ^a   Du, Da Ming ^a,b  

^a PEKING UNIVERSITY   (China)

^b BEIJING INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Amino acids; Catalysis; DBU; Michael addition; Nitroalkene

Indexed keywords

ALKENE DERIVATIVE; AMINO ACID; AROMATIC COMPOUND; GLYCINE DERIVATIVE; GLYCINE IMINE; NITROALKENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 63849333390     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088210     Document Type: Article

References (48)

1. (a) Barrett, G. C. Chemistry and Biochemistry of the Amino Acids; Chapman and Hall: London, 1985.
2. (b) Jones, J. H. Amino Acids and Peptides; RCS: London, 1992.
3. For recent reviews, see: (a) Najera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584.
4. (b) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
5. (c) O'Donnell, M.J. Acc. Chem. Res. 2004, 37, 506.
6. (d) Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518.
7. (e) O'Donnell, M. J. Aldrichimica Ada 2001, 34, 3.
8. (a) O'Donnell, M. J.; Boniece, J. M.;Earp, S.E. Tetrahedron Lett. 1978, 2641.
9. (b) O'Donnell, M. J.; Eckrich, T. M. Tetrahedron Lett. 1978, 4625.
10. (a) Ryoda, A.; Yajima, N.; Haga, T.; Kumamoto, T.; Nakanishi, W.; Kawahata, M.; Yamaguchi, K.; Ishikawa, T. J. Org. Chem. 2008, 73, 133.
11. (b) Saito, S.; Tsubogo, T.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 5364.
12. (c) Reddy, V. J.; Roforth, M. M.; Tan, C.; Reddy, M. V. R. Inorg. Chem. 2007, 46, 381.
13. (d) Arai, S.; Takahashi, F.; Tsuji, R.; Nishida, A. Heterocycles 2006, 67, 495.
14. (e) Chinchilla, R.; Mazón, P.; Nájera, C.; Ortega, F. J.; Yus, M. ARKIVOC 2005, (vi), 222.
15. (f) Rueffer, M. E.; Fort, L. K.; MacFarland, D. K. Tetrahedron: Asymmetry 2004, 15, 3297.
16. (g) Ohshima, T.; Shibuguchi, T.; Fukuta, Y.; Shibasaki, M. Tetrahedron 2004, 60, 7743.
17. (h) Siebum, A. H. G.; Tsang, R. K. F.; van der Steen, R.; Raap, J.; Lugtenburg, J. Eur. J. Org. Chem. 2004, 4391.
18. (i) Akiyama, T.; Hara, M.; Fuchibe, K.; Sakamoto, S.; Yamaguchi, K. Chem. Commun. 2003, 1734.
19. (j) Corey, E. J.; Noe, M. C. Org. Synth. 2003, 80, 34.
20. (k) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539.
21. (l) Ishikawa, T.; Araki, Y.; Kumamoto, T.; Seki, H.; Fukuda, K.; Isobe, T. Chem. Commun. 2001, 245.
22. (m) O'Donnell, M. J.; Delgado, F.; Dominguez, E.; de Blas, J.; Scott, W. L. Tetrahedron: Asymmetry 2001, 12, 821.
23. (n) Tzalis, D.; Knochel, P. Tetrahedron Lett. 1999, 40, 3685.
24. (o) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347.
25. (p) Lopez, A.; Moreno-Mañas, M.; Pleixats, R.; Roglans, A.; Ezquerra, J.; Pedregal, C. Tetrahedron 1996, 52, 8365.
26. (q) Moreno-Mañas, M.; Pleixats, R.; Roglans, A. Liebigs Ann. 1995, 1807.
27. (a) Arai, S.; Tokumaru, K.; Aoyama, T. Chem. Pharm. Bull. 2004, 52, 646.
28. (b) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2000, 2, 1097.
29. (a) Shibuguchi, T.; Mihara, H.; Kuramochi, A.; Sakuraba, S.; Ohshima, T.; Shibasaki, M. Angew. Chem. Int. Ed. 2006, 45, 4635.
30. (b) Wannaporn, D.; Ishikawa, T. Mol. Diversity 2005, 9, 321.
31. (c) Lygo, B.; Allbutt, B.; Kirton, E. H. M. Tetrahedron Lett. 2005, 46, 4461.
32. (d) Tullis, J. S.; Laufersweiler, M. J.; VanRens, J. C.; Natchus, M. G.; Bookland, R. G.; Almstead, N. G.; Pikul, S.; De, B.; Hsieh, L. C.; Janusz, M. J.; Branch, T. M.; Peng, S. X.; Jin, Y. Y.; Hudlicky, T.; Oppong, K. Bioorg. Med. Chem. Lett. 2001, 11, 1975.
33. The benzaldehyde derived glycine imines have been widely used as precursor of 1,3-dipole in [3+2] reactions. For recent examples, see: (a) Yan, X.-X.; Peng, Q.; Zhang, Y.; Zhang, K.; Hong, W.; Hou, X.-L.; Wu, Y.-D. Angew. Chem. Int. Ed. 2006, 45, 1979.
34. (b) Xue, M.-X.; Zhang, X.-M.; Gong, L.-Z. Synlett 2008, 691.
35. For reviews, see: (a) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
36. (b) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
37. Rowley, M.; Leeson, P. D.; Williams, B. J.; Moore, K. W.; Baker, R. Tetrahedron 1992, 48, 3557.
38. Zindel, J.; de Meijere, A. Synthesis 1994, 190.
39. (a) Ayerbe, M.; Arrieta, A.; Cossio, F. P.; Linden, A. J. Org. Chem. 1998, 63, 1795.
40. (b) Vivanco, S.; Lecea, B.; Arrieta, A.; Prieto, P.; Morao, I.; Linden, A.; Cossio, F. P. J. Am. Chem. Soc. 2000, 122, 6078.
41. Cashin, A. L.; Torrice, M. M.; McMenimen, K. A.; Lester, H. A.; Dougherty, D. A. Biochemistry 2007, 46, 630.
42. (a) Lu, S.-F.; Du, D.-M.; Xu, J.; Zhang, S.-W. J. Am. Chem. Soc. 2006, 128, 7418.
43. (b) Lu, S.-F.; Du, D.-M.; Xu, J. Org. Lett. 2006, 8, 2115.
44. (c) Liu, H.; Xu, J.; Du, D.-M. Org. Lett. 2007, 9, 4725.
45. (d) Liu, H.; Lu, S.-F.; Xu, J.; Du, D.-M. Chem. Asian J. 2008, 3, 1111.
46. (e) Zhou, W.-M.; Liu, H.; Du, D.-M. Org. Lett. 2008, 10, 2817.
47. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
48. 4: C, 72.54; H, 6.09; N, 6.51. Found: C, 72.36; H, 6.22; N, 6.35.