Axially chiral guanidine as enantioselective base catalyst for 1,4-addition reaction of 1,3-dicarbonyl compounds with conjugated nitroalkenes

Journal of the American Chemical Society

Volumn 128, Issue 5, 2006, Pages 1454-1455

  Terada, Masahiro ^a   Ube, Hitoshi ^a   Yaguchi, Yusuke ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBONYL DERIVATIVE; GUANIDINE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHIRALITY; CONJUGATION; DERIVATIZATION; ENANTIOSELECTIVITY; HYDROGEN BOND; REACTION ANALYSIS;

ALKENES; GUANIDINE; KETONES; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 32244444791     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja057848d     Document Type: Article

References (33)

1. (a) Hannon, C. L.; Anslyn, E. V. Bioorganic Chemistry Frontiers; Springer-Verlag: Berlin, 1993; Vol. 3. pp 193-255.
2. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
3. Yamamoto, Y.; Kojima, S. In The Chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons Inc.: New York, 1991; Vol. 2, pp 485-526.
4. For reviews, see: (a) Ishikawa, T.; Isobe, T. Chem.-Eur. J. 2002, 8, 552-557.
5. (b) Ishikawa, T.; Isobe, T. J. Synth. Org. Chem. Jpn. 2003, 61, 58-66.
6. (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
7. (b) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis: From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis; Wiley-VCH: Weinheim, Germany. 2005.
8. (c) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719-724.
9. (d) Hayashi, Y. J. Synth. Org. Chem. Jpn. 2005, 63, 464-477.
10. For some excellent studies describing enantioselective catalysis by chiral guanidine bases, see: (a) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911.
11. (b) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157-160.
12. (c) Ishikawa, T.; Araki, Y.; Kumamoto, T.; Seki, H.; Fukuda, K.; Isobe, T. Chem. Commun. 2001, 245-246.
13. (d) Kita, T.; Georgieva, A.; Hasahimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832-2834.
14. (e) Allingham, M. T.; Howard-Jones, A.; Murphy, P. J.; Thomas, D. A.; Caulkett, P. W. R. Tetrahedron Lett. 2003, 44, 8677-8680.
15. (a) Chinchilla, R.; Najera, C.; Sanchez-Agullo, P. Tetrahedron: Asymmetry 1994, 5, 1393-1402.
16. (b) Isobe, T.; Fukuda, K.; Ishikawa, T. Tetrahedron: Asymmetry 1998, 9, 1729-1735.
17. (c) Ma, D.; Cheng, K. Tetrahedron: Asymmetry 1999, 10, 713-719.
18. (d) Isobe, T.; Fukuda, K.; Araki, Y.; Ishikawa, T. Chem. Commun. 2001, 243-244.
19. (e) McManus, J. C.; Carey, J. S.; Taylor, R. J. K. Synlett 2003, 365-368.
20. (f) McManus, J. C.; Genski, T.; Carey, J. S.; Taylor, R. J. K. Synlett 2003, 369-371.
21. For axially chiral guanidines as recognition elements, see: Clews, J.; Curtis, A. D. M.; Malkin, H. Tetrahedron 2000, 56, 8735-8746.
22. For organocatalytic 1,4-addition reactions of nitroalkenes with malonates, see: (a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672-12673.
23. (b) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906-9907.
24. (c) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119-125.
25. (d) Hoashi, Y.; Yabuta, T.; Takemoto, Y. Tetrahedron Lett. 2004, 45, 9185-9188.
26. (e) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105-108.
27. (f) McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367-6370.
28. (g) Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481-4483.
29. For metal-based catalytic 1,4-addition reactions of nitroalkenes with malonates, see: (a) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215-10216.
30. (b) Barnes, D. M.; Ji, J.; Fickes, M. G.; Fitzgerald, M. A.; King, S. A.; Morton, H. E.; Plagge, F. A.; Preskill, M.; Wagaw, S. H.; Wittenberger, S. J.; Zhang, J. J. Am. Chem. Soc. 2002, 124, 13097-13105.
31. (c) Watanabe, M.; Ikagawa, A.; Wang, H.; Murata, K.; Ikariya, T. J. Am. Chem. Soc. 2004, 126, 11148-11149.
32. (d) Evans, D. A.; Seidel, D. J. Am. Chem. Soc. 2005, 127, 9958-9959.
33. During the preparation of this paper, Connon et al. (ref 8f) reported the enantioselective 1,4-addition reactions catalyzed by (thio)urea derivatives of cinchona alkaloids as a highly active organocatalyst. Even by using 5 mol % of this (thio)urea catalyst, more than 6 days are required for conversion of the hindered cyclohexyl-substituted nitroalkene to 4p in an acceptable yield.