Organocatalytic and stereoselective [3 + 2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes

Advanced Synthesis and Catalysis

Volumn 348, Issue 14, 2006, Pages 1818-1822

  Chen, Wei ^a   Yuan, Xiang Hong ^a   Li, Rui ^b   Du, Wei ^a   Wu, Yong ^a   Ding, Li Sheng ^b   Chen, Ying Chun ^a  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

Azomethine imines; Bipyrazolidin 3 one; Diarylprolinols; Dipolar cycloaddition; Organocatalysis; Unsaturated aldehydes

Indexed keywords

EID: 33749348910     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606102     Document Type: Article

References (48)

1. a) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724;
2. b) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
3. for a special issue on organocatalysts, see: Acc. Chem. Res. 2004, 37, No. 8.
4. For a recent review, see: B. List, Chem. Commun. 2006, 819-824.
5. a) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244;
6. b) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458-2460;
7. c) R. M. Wilson, W. S. Jen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 11616-11617;
8. d) K. Ishihara, K. Nakano, J. Am. Chem. Soc. 2005, 127, 10504-10505;
9. e) M. Lemay, W. W. Ogilvie, Org. Lett. 2005, 7, 4141-4144;
10. f) S. A. Selkälä, A. M. P. Koskinen, Eur. J. Org. Chem. 2005, 1620-1624;
11. g) S. A. Selkälä, J. Tois, P. M. Pihko, A. M. P. Koskinen, Adv. Synth. Catal. 2002, 344, 941-945;
12. h) V. Jurcik, R. Wilhelm, Org. Biomol. Chem. 2005, 3, 239-244.
13. For recent reviews, see: a) K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-910;
14. b) K. V. Gothelf, K. A. Jørgensen, Chem. Commun. 2000, 1449-1458;
15. for a highlight, see: c) C. Nájera, J. M. Sansano, Angew. Chem. Int. Ed. 2005, 44, 6272-6276;
16. for recent examples, see: d) T. Kano, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 2174-2175;
17. e) M. P. Sibi, L. M. Stanley, C. P. Jasperse, J. Am. Chem. Soc. 2005, 127, 8276-8277;
18. f) S. Cabrera, R. G. Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2005, 127, 16394-16395;
19. g) S. Shirakawa, P. J. Lombardi, J. L. Leighton, J. Am. Chem. Soc. 2005, 127, 9974-9975;
20. h) T. Kano, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 11926-11927;
21. i) A. S. Gothelf, K. V. Gothelf, R. G. Hazell, K. A. Jørgensen, Angew. Chem. Int. Ed. 2002, 41, 4236-4238;
22. j) J. M. Longmire, B. Wang, X. Zhang, J. Am. Chem. Soc. 2002, 124, 13400-13401.
23. W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875.
24. For other limited examples, see: a) S, Karlsson, H.-E. Högberg, Tetrahedron: Asymmetry 2002, 13, 923-926;
25. b) S. Karlsson, H.-E. Högberg, Eur. J. Org. Chem. 2003, 2782-2791.
26. J.-W. Xie, L. Yue, D. Xue, X.-L. Ma, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Chem. Commun. 2006, 1563-1565.
27. a) H. Dorn, A. Otto, Chem. Ber. 1968, 101, 3287-3301;
28. b) H. Dorn, A. Otto, Angew. Chem. Int. Ed. Engl. 1968, 7, 214-215;
29. c) H. Dorn, A. Otto, Angew. Chem. Int. Ed. Engl. 1968, 7, 888-889.
30. a) L. N. Jungheim, S. K. Sigmund, J. Org. Chem. 1987, 52, 4007-4013;
31. b) J. M. Indelicate, C. E. Pasini, J. Med. Chem. 1988, 37, 1227-1230;
32. c) R. E. Holmes, D. A. Neel, Tetrahedron Lett. 1990, 31, 5567-5570.
33. a) T.-H. Chuang, K. B. Sharpless, Helv. Chim. Acta 2000, 83, 1734-1743;
34. b) I. Panfil, Z. Urbańczyk-Lipkowska, K. Sunwińska, J. Solecka, M. Chmielewski, Tetrahedron 2002, 58, 1199-1212;
35. c) L. Pezdirc, V. Jovanovski, D. Bevk, R. Jakše, S. Pire, A. Meden, B. Stanovnik, J. Svete, Tetrahedron 2005, 61, 3977-3990, and references cited therein.
36. a) R. Shintani, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 10778-10779;
37. b) A. Suárez, C. W. Downey, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 11244-11245.
38. [11a]
39. The cycloaddition of azomethine imine and α,β-unsaturated aldehyde could occur in the absence of catalyst (< 20% yield in 12 h at ambient temperature).
40. For recent examples using chiral α,α-diarylprolinol ethers as organocatalysts, see: a) J. Franzen, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjarsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296-18304;
41. b) Y. Chi, S. H. Gellman, Org. Lett. 2005, 7, 4253-4256;
42. c) M. Marigo, J. Franzen, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 6964-6965;
43. d) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. Int. Ed. 2005, 44, 4212-4215;
44. e) M. Marigo, T. Schulte, J. Franzen, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15710-15711.
45. K. Nakano, K. Nozaki, T Hiyama, J. Am. Chem. Soc. 2003, 125, 5501-5510.
46. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. Int. Ed. 2005, 44, 794-797.
47. 4.
48. C.-Y. Ho, Y.-C. Chen, M.-K. Wong, D. Yang, J. Org. Chem. 2005, 70, 898-906.