Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Brønsted acid: Effect of the additive on the enantioselectivity

Synlett

Volumn , Issue 1, 2006, Pages 141-143

  Akiyama, Takahiko ^a   Tamura, Yukio ^a   Itoh, Junji ^a   Morita, Hisashi ^a   Fuchibe, Kohei ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Aza Diels Alder reaction; Chiral Br Nsted acid; Danishefsky's diene

Indexed keywords

ACID; ALKADIENE; BRONSTED ACID; PHOSPHORIC ACID; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 30544453001     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jcis.2006.03.066     Document Type: Article

References (36)

1. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999.
2. For a review, see: Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
3. (a) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
4. (b) McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094.
5. (c) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
6. (d) Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 3418.
7. (e) McDougal, N. T.; Trevellini, W. L.; Rodgen, S. A.; Kliman, L. T.; Schaus, S. E. Adv. Synth. Catal. 2004, 346, 1231.
8. (f) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature (London) 2003, 424, 146.
9. (g) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5846.
10. (h) Du, H.; Zhao, D.; Ding, K. Chem.-Eur. J. 2004, 10, 5964.
11. (i) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 1080.
12. (j) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. J. Am. Chem. Soc. 2005, 127, 1336.
13. (k) Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680.
14. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.
15. For a chiral phosphoric acid derived from TADDOL, see: Akiyama, T.; Saitoh, Y.; Morita, H.; Fuchibe, K. Adv. Synth. Catal. 2005, 347, 1523.
16. Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. Org. Lett. 2005, 7, 2583.
17. For the use of chiral phosphoric acid as Brønsted acid catalyst, see also: (a) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
18. (b) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804.
19. (c) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2005, 127, 9360.
20. (d) Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Boite, M. Org. Lett. 2005, 7, 3781.
21. Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002.
22. Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807.
23. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
24. (a) Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357.
25. (b) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem. Int. Ed. 1998, 37, 979.
26. (c) Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220.
27. (d) Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225.
28. (e) Kobayashi, S.; Ueno, M.; Saito, S.; Mizuki, Y.; Ishitani, H.; Yamashita, Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5476.
29. (f) Yamashita, Y.; Mizuki, Y.; Kobayashi, S. Tetrahedron Lett. 2005, 46, 1803.
30. Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem. Int. Ed. 1998, 37, 3121.
31. Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018.
32. Mancheño, O. G.; Arrayás, R. G.; Carretero, J. C. J. Am. Chem. Soc. 2004, 126, 456.
33. For Brønsted acid catalyzed aza-Diels-Alder reaction, see: Akiyama, T.; Takaya, J.; Kagoshima, H. Tetrahedron Lett. 1999, 40, 7831.
34. Yuan, Y.; Li, X.; Ding, K. Org. Lett. 2002, 4, 3309.
35. The nine-membered cyclic structure of the complex was observed as an energy minimum by quantum chemical calculations (PM3, Spartan '02, Wavefunction, Inc.).
36. At present, the role of the protic additive is not clear. For the improvement of the enantioselectivity by use of alcohol as a mixed solvent, see: Beeson, T. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 8826.