Design of chiral N-triflyl phosphoramide as a strong chiral Brønsted acid and its application to asymmetric Diels-Alder reaction

Journal of the American Chemical Society

Volumn 128, Issue 30, 2006, Pages 9626-9627

  Nakashima, Daisuke ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; PHOSPHORAMIDIC ACID DERIVATIVE; SILANE DERIVATIVE;

AMIDATION; ARTICLE; CATALYSIS; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 33746654536     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062508t     Document Type: Article

References (49)

1. For reviews, see: (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
2. (b) Seayad, J.; List, B. Org. Biomol. Chem. 2003, 3, 719.
3. (c) Pihko, P. M.; Angew. Chem., Int. Ed. 2004, 43, 2062.
4. (d) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520.
5. (a) Burk, P.; Koppel, I. A.; Koppel, I.; Yagupolskii, L. M.; Taft, R. W. J. Comput. Chem. 1996, 17, 30.
6. (b) Leito, I.; Kaljurand, I.; Koppel, I. A.; Yagupolskii, L. M.; Vlasov, V. M. J. Org. Chem. 1998, 63, 7868.
7. (c) Koppel, I. A.; Koppel, J.; Leito, I.; Koppel, I.; Mishima, M.; Yagupolskii, L. M. J. Chem. Soc., Perkin Trans. 2 2001, 229.
8. (d) Yagupolskii, L. M.; Petrik, V. N.; Kondratenko, N. V.; Sooväli, L.; Kaljurand, I.; Leito, I.; Koppel, I. A. J. Chem. Soc., Perkin Trans. 2 2002, 1950.
9. Chiral phosphoric acid: (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
10. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
11. (c) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804.
12. (d) Uraauchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2005, 127, 9360.
13. (e) Akiyama, T.; Saitoh, Y.; Morita, H.; Fuchibe, K. Adv. Synth. Catal. 2005, 347, 1523.
14. (f) Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. Org. Lett. 2005, 7, 2583.
15. (g) Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. J. Am. Chem. Soc. 2005, 127, 15696.
16. (h) Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Bolte, M. Org. Lett. 2005, 7, 3781.
17. (i) Hoffman, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424.
18. (J) Terada, M.; Sorimachi, K.; Uraguchi, D. Synlett 2006, 133.
19. (k) Akiyama, T.; Tamura, Y.; Itoh, J.; Morita, H.; Fuchibe, K. Synlett 2006, 141.
20. (l) Storer, R. I.; Carrera, D. E.; Ni, Y.; Macmillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
21. (m) Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
22. (n) Rueping, M.; Sugiono, E.; Azap, C. Angew. Chem., Int. Ed. 2006, 45, 2617.
23. (o) Terada, M.; Machida, K.; Sorimachi, K. Angew. Chem., Int. Ed. 2006, 45, 2254.
24. 4 (7.21 and 12.31. respectively): Burlingham, B. T.; Widlanski, T. S. J. Org. Chem. 2001, 66, 7561.
25. Asymmetric Diels-Alder reaction of ketone: (a) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992.
26. (b) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
27. (c) Hawkins, J. M.; Nambu, M.; Loren, S. Org. Lett. 2003, 5, 4293.
28. (d) Hu, Q.-Y.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 13708.
29. (e) Ryu, D. H.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 4800.
30. (f) Futatsugi, K.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 1484.
31. (g) Singh, R. S.; Harada, T. Eur. J. Org. Chem. 2005, 3433.
32. Another approach for the asymmetric Diels-Alder reaction of ketone: Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
33. Nakashima, D.; Yamamoto, H. Org. Lett. 2005, 7, 1251.
34. Asymmetric Diels-Alder reaction catalyzed by chiral Brønsted acid: (a) Schuster, T.; Bauch, M.; Dülrner, G.; Göbel, M. W. Org. Lett. 2000, 2, 179.
35. (b) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
36. (c) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5846.
37. (d) Du, H.; Zhao, D.; Ding, K. Chem.-Eur. J. 2004, 10, 5964.
38. (e) Tonoi, T.; Mikami, K. Tetrahedron Lett. 2005, 46, 6355.
39. (f) Zhuang, W.; Poulsen, T. B.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 3284.
40. (g) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. J. Am. Chem. Soc. 2005, 127, 1336.
41. (h) Rajaram, S.; Sigman, M. S. Org. Lett. 2005, 7, 5473.
42. (i) Zhang, X.; Du, H.; Wang, Z.; Wu, Y.-D.; Ding, K. J. Org. Chem. 2006, 7l, 2862.
43. When methyl vinyl ketone was used instead of ethyl vinyl ketone, enantioselectivity decreased to 48% ee.
44. 1H NMR.
45. Our contribution to the silyl cation chemistry: (a) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851.
46. (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564.
47. (c) Hasegawa, A.; Ishihara, K.; Yamamoto, H. Angew. Chem., Int. Ed. 2003, 42, 5731.
48. (d) Boxer, M. B.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 48.
49. TBS enol ether is more reactive than TIPS enol ether: Mayr, H.; Kempf. B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66.