A mild and efficient aza-Diels-Alder reaction of N-benzhydryl imines with trans-1-methoxy-1-methyl-3-trimethylsiloxybuta-1,3-diene catalyzed by Yb(OTf)3

Tetrahedron

Volumn 61, Issue 40, 2005, Pages 9594-9599

  Cheng, Ke ^a   Lin, Lili ^a   Chen, Shikui ^a   Feng, Xiaoming ^a  

^a China   (China)

Author keywords

Cycloaddition; N Benzhydryl imines; Nitrogen heterocycles; Ytterbium

Indexed keywords

1 BENZHYDRYL 5 METHYL 2 (2 CHLOROPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (2 FURYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (2 METHOXYPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (2 METHYLPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (2 PYRIDYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (3 CHLOROPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (3 METHOXYPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (3 METHYLPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (3,4 METHYLENEDIOXYPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (4 CHLOROPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (4 FLUOROPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (4 METHOXYPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 (4 METHYLPHENYL) 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 CYCLOHEXYL 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 ISOPROPYL 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 PHENYL 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 PROPYL 2,3 DIHYDRO 4 1H PYRIDONE; 1 BENZHYDRYL 5 METHYL 2 STYRYL 2,3 DIHYDRO 4 1H PYRIDONE; 1 METHOXY 2 METHYL 3 TRIMETHYLSILOXYBUTA 1,3 DIENE; ALDEHYDE DERIVATIVE; ALKADIENE; AMINE; HETEROCYCLIC COMPOUND; IMINE; LEWIS ACID; N BENZHYDRYL IMINE; PYRIDONE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; PRIORITY JOURNAL;

BETULACEAE;

EID: 27744456022     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.082     Document Type: Article

References (40)

1. (a) Waldmann, H. Organic Synthesis Highlight, 2nd ed.; VCH: Weinheim, 1995; p 37.
2. (b) Weinreb, S. M. In Trost, B. M., Fleming, I., Semmelhock, M. F., Eds.; Comprehensive Organic Synthesis; Pergamon: Oxford, 1991; Vol. 5, Chapters 2 and 9, p 401.
3. (c) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, CA, 1987.
4. For review: (a) Rubiralta, M.; Giralt, E.; Diez, A. Piperidine: Structure, Preparation, and Synthetic Applications of Piperidine and Its Derivatives; Elsevier: Amsterdam, 1991.
5. (b) Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633-640.
6. (a) Patmore, N. J.; Hague, C.; Cotgreave, J. H.; Mahon, M. F.; Frost, C. G.; Weller, A. S. Chem. Eur. J. 2002, 8, 2088-2098.
7. (b) Collin, J.; Jaber, N.; Lannou, M. I. Tetrahedron Lett. 2001, 42, 7405-7407.
8. (c) Laurent-Robert, H.; Garrigues, B.; Dubac, J. Synlett 2000, 1160-1162.
9. (d) Ali, T.; Chauhan, K. K.; Frost, C. G. Tetrahedron Lett. 1999, 40, 5621-5624.
10. (e) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195-1202.
11. (f) Bari, L. D.; Guillarme, S.; Hermitage, S.; Howard, J. A. K.; Jay, D. A.; Pescitelli, G.; Whiting, A.; Yufit, D. S. Synlett 2004, 708-710.
12. (g) Hattori, K.; Yamamoto, H. Synlett 1993, 129-130.
13. (h) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233-234.
14. Morgan, P. E.; McCague, R.; Whiting, A. J. Chem. Soc., Perkin Trans. 1 2000, 515-525.
15. (j) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524.
16. With a solid catalyst: (a) Kumareswaran, R.; Reddy, B. G.; Vankar, Y. D. Tetrahedron Lett. 2001, 42, 7493-7495.
17. (b) Wang, Y.; Wilson, S. R. Tetrahedron Lett. 1997, 38, 4021-4024.
18. For inverse electron demand aza-Diels-Alder reactions: (a) Sundararajan, G.; Prabagaran, N.; Varghese, B. Org. Lett. 2001, 13, 1973-1976.
19. (b) Yadav, J. S.; Subba, B. V.; Srinivas, R.; Madhuri, Ch.; Ramalingam, T. Synlett 2001, 240-242.
20. Aza-Diels-Alder reactions in MeOH without catalyst: Yuan, Y.; Li, X.; Ding, K. Org. Lett. 2002, 4, 3309-3311.
21. 2O: (a) Loncaric, C.; Manabe, K.; Kobayashi, S. Chem. Commun. 2003, 574-575.
22. (b) Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475-477.
23. (c) Lock, R.; Waldmann, H. Tetrahedron Lett. 1996, 37, 2753-2756.
24. Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264-3265.
25. (a) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979-981.
26. (b) Kobayashi, S.; Kusakabe, K.-i.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221.
27. (c) Kobayashi, S.; Kusakabe, K.-i.; Komiyama, S.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227.
28. (d) Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357-7360.
29. (e) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
30. (a) Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 3121-3124.
31. (b) Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
32. (c) Jørgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558-3588.
33. (d) Buonora, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099-6138.
34. Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018-4019.
35. Mancheño, O. G.; Arrayás, R. G.; Carretero, J. C. J. Am. Chem. Soc. 2004, 126, 456-457.
36. (a) Guillarme, S.; Whiting, A. Synlett 2004, 711-713.
37. (b) Bromidge, S.; Wilson, P. C.; Whiting, A. Tetrahedron Lett. 1998, 39, 8905-8908.
38. (c) Bundu, A.; Guillarme, S.; Hannan, J.; Wan, H.; Whiting, A. Tetrahedron Lett. 2003, 44, 7849-7850.
39. Cheng, K.; Zeng, B.; Yu, Z.; Gao, B.; Feng, X. Synlett 2005, 1018-1020.
40. Kerwin, J. F., Jr.; Danishefsky, S. Tetrahedron Lett. 1982, 23, 3739-3742.