Organocatalytic entry into 2,6-disubstituted aza-Achmatowicz piperidinones: Application to (-)-sedacryptine and its epimer

Organic Letters

Volumn 16, Issue 7, 2014, Pages 2038-2041

  Van Der Pijl, Ferdi ^a   Harmel, Robert K ^a   Richelle, Gaston J J ^a   Janssen, Peter ^a   Van Delft, Floris L ^a   Rutjes, Floris P J T ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ORGANOSILICON DERIVATIVE; PIPERIDONE DERIVATIVE; SEDACRYPTINE;

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

ALKALOIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; PIPERIDONES; STEREOISOMERISM;

EID: 84898726621     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500633u     Document Type: Article

References (25)

1. Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1986; Vol. 26, p 89.
2. OHagan, D. Nat. Prod. Rep. 2000, 17, 435-446
3. Wijdeven, M. A.; Willemsen, J.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2010, 2831-2844
4. Wijdeven, M. A.; van den Berg, R. J. F.; Wijtmans, R.; Botman, P. N. M.; Blaauw, R. H.; Schoemaker, H. E.; van Delft, F. L.; Rutjes, F. P. J. T. Org. Biomol. Chem. 2009, 7, 2976-2980
5. For a review, see: Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105-114
6. Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2008, 37, 29-41
7. Verkade, J. M. M.; van der Pijl, F.; Willems, M. A. J. H. P.; Quaedflieg, P. J. L. M.; van Delft, F. L.; Rutjes, F. P. J. T. J. Org. Chem. 2009, 74, 3207-3210
8. Vesely, J.; Rios, R. Chem. Soc. Rev. 2014, 43, 611-630
9. Vesely, J.; Rios, R.; Ibrahem, I.; Cordova, A. Tetrahedron Lett. 2007, 48, 421-425
10. Yang, J. W.; Stadler, M.; List, B. Angew. Chem., Int. Ed. 2007, 46, 609-611
11. Yang, J. W.; Stadler, M.; List, B. Nat. Protoc. 2007, 2, 1937-1942
12. Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964-12965
13. Haukaas, M. H.; ODoherty, G. A. Org. Lett. 2001, 3, 401-404
14. Crystal structure data can be obtained free from charge via the Internet at www.ccdc.cam.ac.uk/conts/retreiving.html (deposition no. CCDC 988042).
15. Botman, P. N. M.; Dommerholt, F. J.; de Gelder, R.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T.; Blaauw, R. H. Org. Lett. 2004, 6, 4941-4944
16. Hootelé, C.; Colau, B.; Halin, F.; Declercq, J. P.; Germain, G.; Vanmeerssche, M. Tetrahedron Lett. 1980, 21, 5061-5062
17. Colau, B.; Hootelé, C. Can. J. Chem. 1983, 61, 470-472
18. Natsume, M.; Ogawa, M. Heterocycles 1983, 20, 601-605
19. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517
20. Akiyama, E.; Hirama, M. Synlett 1996, 100-102
21. Plehiers, M.; Hootele, C. Can. J. Chem. 1996, 74, 2444-2453
22. Wee, A. G. H.; Fan, G. J. Org. Lett. 2008, 10, 3869-3872
23. Noutsias, D.; Kouridaki, A.; Vassilikogiannakis, G. Org. Lett. 2011, 13, 1166-1169
24. Adger, B. M.; Barrett, C.; Brennan, J.; Mckervey, M. A.; Murray, R. W. J. Chem. Soc., Chem. Commun. 1991, 1553-1554
25. Pelss, A.; Kumpulainen, E. T. T.; Koskinen, A. M. P. J. Org. Chem. 2009, 74, 7598-7601