A novel diastereoselective multicomponent cascade reaction

Organic Letters

Volumn 12, Issue 10, 2010, Pages 2230-2233

  Kriis, Kadri ^a   Ausmees, Kerti ^a   Pehk, Tõnis ^b   Lopp, Margus ^a   Kanger, Tõnis ^a  

^a TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^b NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77952368074     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1005714     Document Type: Article

References (37)

1. Marek, I. Chem.- Eur. J. 2008, 14, 7460-7468
2. Ugi, I.; Stainbrückner, C. Chem.Ber. 1961, 94, 2802-2814
3. Ugi, I.; Offermann, K. Chem.Ber 1964, 97, 2996-3007
4. Gokel, G.; Lüdke, G.; Ugi, I. In Isonitrile Chemistry; Ugi, I., Ed.; Academic Press: London, 1971; pp 145 - 215.
5. Recent reviews of multicomponent reactions
6. Sunderhaus, J. D.; Martin, S. F. Chem.- Eur. J. 2009, 15, 1300-1308
7. Ganem, B. Acc. Chem. Res. 2009, 42, 463-472
8. Tietze, L. F.; Kinzel, T.; Brazel, C. C. Acc. Chem. Res. 2009, 42, 367-378
9. Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602-1634
10. Dömling, A. Chem. Rev. 2006, 106, 17-89
11. Recent reviews of domino reactions
12. Enders, D.; Narine, A. A. J. Org. Chem. 2008, 73, 7857-7870
13. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581
14. Tietze, L. F. Chem. Rev. 1996, 96, 115-136
15. Padwa, A.; Bur, S. K. Tetrahedron 2007, 63, 5341-5378
16. Laars, M.; Ausmees, K.; Uudsemaa, M.; Tamm, T.; Kanger, T.; Lopp, M. J. Org. Chem. 2009, 74, 3772-3775
17. Laars, M.; Kriis, K.; Kailas, T.; Müürisepp, A.-M.; Pehk, T.; Kanger, T.; Lopp, M. Tetrahedron: Asymmetry 2008, 19, 641-645
18. Kanger, T.; Kriis, K.; Laars, M.; Kailas, T.; Müürisepp, A.-M.; Pehk, T.; Lopp, M. J. Org. Chem. 2007, 72, 5168-5173
19. Mossé, S.; Laars, M.; Kriis, K.; Kanger, T.; Alexakis, A. Org. Lett. 2006, 8, 2559-2562
20. Li, H.; Zu, L.; Xie, H.; Wang, J.; Wang, W. Chem. Commun. 2008, 5636-5638
21. Drescher, K.; Haupt, A.; Unger, L.; Turner, S. C.; Braje, W.; Grandel, R. Chem. Abstr. 2006, 144, 390732; PCT Int. Appl.WO 2006040176
22. Sosunov, E. A.; Gainullin, R. Z.; Danilo, P., Jr.; Anyukhovsky, E. P.; Kirchengast, M.; Rosen, M. R. J. Pharm. Exp. Ther. 1999, 290, 146-152
23. Graul, A.; Castaner, J. Drugs Future 1998, 23, 370-373
24. Hasinoff, B. B.; Creighton, A. M.; Kozlowska, H.; Thampatty, P.; Allan, W. P.; Yalowich, J. C. Mol. Pharmacol. 1997, 52, 839-845
25. Miesch, M. Curr. Org. Synth. 2006, 3, 327-340
26. For iminium ion activation, see
27. Erkkila, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416-5470
28. Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328-9329
29. Photochemical cycloaddition leading to disubstituted 3-azabicyclo[3.2.0] heptane
30. Bach, T.; Krüger, C.; Harms, K. Synthesis 2000, 305-320
31. Bach, T.; Pelkmann, C.; Harms, K. Tetrahedron Lett. 1999, 40, 2103-2104
32. 4.
33. Recent review of organocatalytic aza-Michael reaction
34. Enders, D.; Wang, C.; Liebich, J. X. Chem.- Eur. J. 2009, 15, 11058-11076
35. Bouwkamp, M. W.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13340-13341
36. Seidl, P. R. The Chemistry of Cyclobutanes; John Wiley & Sons: New York, 2005; p 213.
37. Whitesell, J. K.; Minton, M. Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy; Chapman and Hall: New York, 1987.