Catalytic imino Diels-Alder reaction by triflic imide and its application to one-pot synthesis from three components

Tetrahedron

Volumn 62, Issue 51, 2006, Pages 11900-11907

  Takasu, Kiyosei ^a   Shindoh, Naoya ^a   Tokuyama, Hidetoshi ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Imino Diels Alder reaction; Substituted piperidines; Three component reaction; Triflic imide

Indexed keywords

ALKENE DERIVATIVE; IMIDE; IMINE; IMINO ACID; INDOLE; PIPERIDONE DERIVATIVE; PYRIDINE;

ARTICLE; CATALYSIS; CONFORMATION; DIELS ALDER REACTION; PRIORITY JOURNAL; SOLID STATE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BETULACEAE;

EID: 33750742208     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.092     Document Type: Article

References (39)

1. Elbein D.A., and Molyneux R. In: Palletier S.W. (Ed). Alkaloids; Chemical and Biological Perspectives Vol. 57 (1987), Wiley, New York, NY
2. O'Hagan D. Nat. Prod. Rep. 17 (2000) 435-446
3. Boger D.L., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic, San Diego
4. Heintzelman G.R., Meigh I.R., Mehajan Y.R., and Weinreb S.M. Org. React. 65 (2005) 141-599
5. Buonora P., Olsen J.-C., and Oh T. Tetrahedron 57 (2001) 6099-6138
6. Jayakumar S., Ishar M.P.S., and Mahajan M.P. Tetrahedron 58 (2002) 379-471
7. Takasu K., Nishida N., Tomimura A., and Ihara M. J. Org. Chem. 70 (2005) 3957-3962
8. Danishefsky S., and Kitahara T. J. Am. Chem. Soc. 96 (1974) 7807-7808
9. For selected examples:
10. Hermitage S., Howard J.A.K., Jay D., Pritchard R.G., Probert M.R., and Whiting A. Org. Biomol. Chem. 2 (2004) 2451-2460
11. Badorrey R., Cativiela C., Dfaz-de-Villegas M.D., and Galvez J.A. Tetrahedron 55 (1999) 7601-7612
12. For selected examples:
13. Akiyama T., Takaya J., and Kagoshima H. Tetrahedron Lett. 40 (1999) 7831-7834
14. Itoh J., Fuchibe K., and Akiyama T. Angew. Chem., Int. Ed. 45 (2006) 4796-4798
15. Akiba K., Motoshima T., Ishimaru K., Yabuta K., Hirota H., and Yamamoto Y. Synlett (1993) 657-658
16. Stanetty P., Mihovilovic M.D., Mereiter K., Völlenkle H., and Renz F. Tetrahedron 54 (1998) 875-894
17. Ishimaru K., and Kojima T. J. Chem. Soc., Perkin Trans. 1 (2000) 2105-2108
18. Ishimaru K., and Kojima T. Heterocycles 55 (2001) 1591-1597
19. For a related study using 2-amino-1,3-siloxybutadiene instead of 1-siloxy-1,3-butadiene;. Barluenga J., Alejandro F., Aznar F., and Valdés C. Tetrahedron Lett. 43 (2002) 8159-8163
20. Ishimaru et al. reported the reaction of aldimines with 2-siloxybutadienes in the presence of triflic acid (TfOH) as a Brønsted acid catalyst furnished Mannich adduct. On the other hand, in our case using triflic imide, no Mannich adduct was observed. Ishimaru K., and Kojima T. Tetrahedron Lett. 44 (2003) 5441-5444
21. Rameshkumar N., Veena A., Ilavarasan R., Adirai M., Shanmugapandivan P., and Sridhar S.K. Biol. Pharm. Bull. 26 (2003) 188-193
22. Ramalingan C., Balasubramanian S., Kabilan S., and Vasudevan A. Eur. J. Med. Chem. 39 (2004) 527-533
23. Soldatenkov A.T., Lenov A.N., Mamybekova Z.A., Kolyadina N.M., Mobio I.G., Naumov Y.I., Kumarova A.O., and An L.T. Pharm. Chem. J. 38 (2004) 361-363
24. Aridoss G., Balasubtamanian S., Parthiban D., and Kabilan S. Eur. J. Med. Chem. 41 (2006) 268-275
25. Inanaga K., Takasu K., and Ihara M. J. Am. Chem. Soc. 127 (2005) 3668-3669
26. Takasu K., Hosokawa N., Inanaga K., and Ihara M. Tetrahedron Lett. 47 (2006) 6053-6056
27. Takasu, K.; Inanaga, K.; Ihara, M. unpublished results.
28. 2NH-catalyzed reactions;
29. Athman R.B., Bousquet T., Othman M., and Della V. Org. Lett. 7 (2005) 5335-5337
30. Boxer M., and Yamamoto H. J. Am. Chem. Soc. 128 (2006) 48-49
31. Sweis R.F., Schramm S.A., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 7442-7443
32. Ishihara K., Hiraiwa Y., and Yamamoto H. Synlett (2001) 1851-1854
33. Foropoulos Jr. J., and DesMarteau D.D. Inorg. Chem. 23 (1984) 3720-3723
34. For examples of three component synthesis, see:
35. Kobayashi S., Ishitani H., and Nagayama S. Chem. Lett. (1995) 423-424
36. Sisko J., and Weinreb S.M. Tetrahedron Lett. 30 (1989) 3037-3040
37. 18 we attempted the imino Diels-Alder variant starting from siloxydienes 1, imines 2, and acrylates (Scheme 6). Unfortunately, the desired MCR adduct 8 could not be obtained under various reaction conditions.
38. Inanaga K., Takasu K., and Ihara M. J. Am. Chem. Soc. 126 (2004) 1352-1353
39. Ollevier T., and Nadeau E. J. Org. Chem. 69 (2004) 9292-9295