A new organocatalyzed Michael-Michael cascade reaction generates highly substituted fused carbocycles

Organic Letters

Volumn 11, Issue 24, 2009, Pages 5654-5657

  McGarraugh, Patrick G ^a   Brenner, Stacey E ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; KETONE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOBUTANES; KETONES; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; STEREOISOMERISM;

EID: 72849152930     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9024293     Document Type: Article

References (28)

1. For a review. see: Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581.
2. (a) Xie, H.; Zu, L.; Li, H.; Wang, J.; Wang, W. J. Am. Chem. Soc. 2007, 48, 5835-5839.
3. (b) Vesely, J.; Zhao, G.-L.; Bartoszewicz, A.; Córdova, A. Tetrahedron Lett. 2008, 49, 4209-4212.
4. (c) Ibrahem, I.; Zhao, G.-L.; Rios, R.; Vesely, J.: Sundén, H.; Dziedzic, P.: Córdova, A. Chem.-Eur. J. 2008, 14, 7867-7879.
5. (a) Mango, M.; Bertelsen, S.; Landa, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 5475-5479.
6. (b) Enders, D.; Narine, A. A.; Benninghaus, T. R.; Raabe. G. Synlett 2007. 1667-1670.
7. (c) Wang, J.; Li, H.; Xie, H.; Zu, L.; Shen, X.: Wang, W. Angew. Chem., Int. Ed. 2007, 46, 9050-9053.
8. (d) Hong, B.-C.; Nimje, R. Y.; Sadani, A. A.; Liao, J.-H. Org. Lett. 2008, 10, 2345-2348.
9. (e) Zhao, G.-L.; Dziedzic, P.; Ullah, F.; Eriksson, L.; Córdova, A. Tetrahedron Lett. 2009, 50, 3458-3462.
10. (f) Rueping, M.; Kuenkel, A.: Tato. F.: Bats, J. W. Angew. Chem., Int. Ed. 2009, 48, 3699-3702.
11. (g) Enders, D.; Wang, C.; Bats, J. W. Synlett 2009, 1777-1780.
12. (a) Havashi, Y.; Toyoshima, M.; Hiroaki, G.; Ishikawa, H. Org. Lett. 2009, 11, 45-48.
13. (b) Lukaz, A.; Richter, B.; Vila, C.; Krawczyk, H.; Jørgensen, K. A. Chem.-Eur. J. 2009, 15, 3093-3102.
14. Ibrahem, I.; Rios, R.; Vesely, J.; Córdova, A. Tetrahedron Lett. 2007, 48, 6252-6257.
15. (a) Hayashi, Y.; Okano, Y.: Aratake, S.; Hazelard, D. Angew. Chem., Int. Ed. 2007, 46, 4922-4925.
16. (b) Reyes, E.; Jiang, H.; Milelli, A.; Eisner, P.; Hazell. R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 9202-9205.
17. Liu, Y.-k.; Ma, C.; Jiang, K.; Liu. T.-Y.; Chen, Y.-C. Org. Lett. 2009, 11, 2848-2851.
18. (a) Enders, D.; Hüettl, M. R. M.; Grondai, C.; Raabe, G. Nature 2006, 441, 861-863.
19. (b) Zu, L.; Li, H.; Xie, H.; Wang, J.; Jiang, W.; Tang, Y.; Wang, W. Angew. Chem., Int. Ed. 2007, 46, 3732-3734.
20. (c) Carlone, A.; Cabrera, S.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1101-1104.
21. (d) Bor-Cheng, H.; Nimje, R. Y.; Wu, M.-F.; Sadani, A. A. Eur. J. Org. Chem. 2008, 1449-1457.
22. (e) Penon, O.; Carlone, A.; Mazzanti, A.; Locatelli, M.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem.-Eur. J. 2008, 14, 4788-4791.
23. (f) Zhao, G.-L.; Ibrahem, I.; Dziedzic, P.; Sun, J.; Bonneau, C.; Córdova, A. Chem. - Eur. J. 2008, 14, 10007-10011.
24. (g) Bencivenni, G.; Wu, L.-Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M.-P.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 1-5.
25. (h) Hong, B.-C.; Nimje, R. Y.; Liao, J.-H. Org. Biomol. Chem. 2009, 3095-3101.
26. For a review of organocatalyzed conjugate addition reactions, including those involving β-dicarbonyl compounds as Michael donors, see Almasi, D.; Alonso, D. A.; Nájera, C. Tetrahedron: Asymmetry 2007, 18, 299-365.
27. Cabrera, S.; Alemán, J.; Bolze, P.; Bertelsen, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2008, 47, 121-125.
28. Zhu, M.-.K.; Wei, Q.; Gong, L.-Z. Adv. Synth. Catal. 2008, 350, 1281-1285.