Organocatalytic asymmetric reaction cascade to substituted cyclohexylamines

Journal of the American Chemical Society

Volumn 129, Issue 24, 2007, Pages 7498-7499

  Zhou, Jian ^a   List, Benjamin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BRONSTED ACID; CYCLOHEXYLAMINE DERIVATIVE; ENAMINE; KETONE DERIVATIVE;

ACETYLATION; AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; HYDROGENATION; MASS SPECTROMETRY; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 34250835001     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072134j     Document Type: Article

References (42)

1. For an excellent review, see: Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
2. (a) List, B. Chem. Commun. 2006, 819.
3. (b) Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 39, 79.
4. (c) Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876.
5. For recent examples, see: (a) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. J. Am. Chem. Soc. 2005, 127, 15036.
6. (b) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
7. (c) Marigo, M.; Schulte, T.; Franzén, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710.
8. (d) Enders, D.; Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861.
9. (e) Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354.
10. (f) Brandau, S.; Maerten, E.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 14986.
11. (g) Enders, D.; Hüttl, M. R. M.; Runsink, J.; Raabe, G.; Wendt, B. Angew. Chem., Int. Ed. 2007, 46, 467.
12. (h) Carlone, A.; Cabrera, S.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1101.
13. (i) Li, H.; Wang, J.; E-Nunu, T.; Zu, L.; Jiang, W.; Wei, S.; Wang, W. Chem. Commun. 2007, 507.
14. Also see: (j) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
15. For reviews, see: (a) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520.
16. (b) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999.
17. (c) Connon, S. J. Angew. Chem., Int. Ed. 2006, 45, 3909.
18. (d) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299.
19. (e) Bolm, C.; Rantanen, T.; Schiffers, I.; Zani, L. Angew. Chem., Int. Ed. 2005, 44, 1758.
20. (f) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
21. For pioneering studies on chiral phosphoric acid catalysis, please see: (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
22. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
23. (a) Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193.
24. (b) Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368.
25. For chiral amine-catalyzed conjugate reductions of α,β- unsaturated carbonyl compounds, see: (a) Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 6660.
26. (b) Yang, J. W.; Hechavarria Fonseca, M. T.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2005, 44, 108.
27. (c) Ouellet, S. G.; Tuttle, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 32.
28. (d) Tuttle, J. B.; Ouellet, S. G.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 12662.
29. (a) Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424.
30. (b) Hoffmann, S.; Nicoletti, M.; List, B. J. Am. Chem. Soc. 2006, 128, 13074.
31. Also see: (c) Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781.
32. (d) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
33. For a review on amine-catalyzed aldol reactions, see: List, B. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 161-200.
34. For a recent non-asymmetric amine-mediated aldol condensation, Pd-catalyzed hydrogenation - reductive amination cascade in the synthesis of Fenpropimorph, see: Forsyth, S. A.; Gunaratne, H. Q. N.; Hardacre, C.; McKeown, A.; Rooney, D. W. Org. Process Res. Dev. 2006, 10, 94.
35. Verkade, J. M. M.; van Hermert, L. J. C.; Quaedflieg, P. J. L. M.; Alsters, P. L.; van Delft, F. L.; Rutjes, F. P. J. T. Tetrahedron Lett. 2006, 47, 8109.
36. Based on a SciFinder survey, there are more than 300 patented structures containing a 3-methylcyclohexylamine moiety. For selected pharmaceutically active compounds incorporating a 3-substituted cyclohexylamine, see: (a) Johnston, T. P.; McCaleb, G. S.; Clayton, S. D.; Frye, J. L.; Krauth, C. A.; Montgomery, J. A. J. Med. Chem. 1977, 20, 279.
37. (b) Palomba, M.; Pau, A.; Boatto, G.; Asproni, B.; Auzzas, L.; Cerri, R.; Arenare, L.; Filippelli, W.; Falcone, G.; Motola, G. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 17.
38. (c) Norman, B. H.; Lander, P. A.; Gruber, J. M.; Kroin, J. S.; Cohen, J. D.; Jungheim, L. N.; Starling, J. J.; Law, K. L.; Self, T. D.; Tabas, L. B.; Williams, D. C.; Paul, D. C.; Dantzig, A. H. Bioorg. Med. Chem. Lett. 2005, 15, 5526.
39. For chiral auxiliary approaches, see: (a) Demailly, G.; Solladie, G. J. Org. Chem. 1981, 46, 3102.
40. (b) Knupp, G.; Frahm, A. W. Arch. Pharm. 1985, 318, 535.
41. Most diketones 1 can be obtained from commercially available lactone 6 or from pyridines 7 (see Supporting Information): (Chemical Equation Presented)
42. As expected, 2,5-diketones gave the corresponding pyrroles.