Enantioselective 1,3-dipolar cycloaddition of nitrones with ethyl vinyl ether: The difference between Brønsted and Lewis acid catalysis

Angewandte Chemie - International Edition

Volumn 47, Issue 13, 2008, Pages 2411-2413

  Jiao, Peng ^a   Nakashima, Daisuke ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Asymmetric catalysis; Cycloaddition; Organocatalysis; Phosphoramides

Indexed keywords

ACIDS; CHEMICAL REACTIONS; DIFFERENCE EQUATIONS; DIFFERENTIATION (CALCULUS); ETHERS; ORGANIC COMPOUNDS;

ASYMMETRIC CATALYSIS; CHEMICAL EQUATIONS; DIPOLAR CYCLOADDITION; ENANTIOSELECTIVE; LEWIS ACID CATALYSIS; NITRONES; ORGANOCATALYSIS; PHOSPHORAMIDES; VINYL ETHERS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

CYCLOADDITION;

EID: 53249085441     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705314     Document Type: Article

References (56)

1. For reviews, see: a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296;
2. b) P. M. Pihko, Angew. Chem. 2004, 116, 2110-2113;
3. Angew. Chem. Int. Ed. 2004, 43, 2062-2064;
4. c) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724;
5. d) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573;
6. Angew. Chem. Int. Ed. 2006, 45, 1520-1543;
7. e) S. J. Connon, Angew. Chem. 2006, 118, 4013-4016;
8. Angew. Chem. Int. Ed. 2006, 45, 3909-3912;
9. f) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010.
10. Chiral phosphoric acid catalyzed reactions: a) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357;
11. b) D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804-11805;
12. c) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594;
13. Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
14. d) D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2005, 127, 9360-9361;
15. e) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696-15697;
16. f) S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590-7593;
17. Angew. Chem. Int. Ed. 2005, 44, 7424-7427;
18. g) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86;
19. h) J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086-1087;
20. i) T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070-13071;
21. j) S. Hoffmann, M. Nicoletti, B. List, J. Am. Chem. Soc. 2006, 128, 13074-13075;
22. k) M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2006, 118, 2312-2315;
23. Angew. Chem. Int. Ed. 2006, 45, 2254-2257;
24. l) M. Rueping, E. Sugiono, C. Azap, Angew. Chem. 2006, 118, 2679-2681;
25. Angew. Chem. Int. Ed. 2006, 45, 2617-2619;
26. m) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765-3768;
27. Angew. Chem. Int. Ed. 2006, 45, 3683-3686;
28. n) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914-4916;
29. Angew. Chem. Int. Ed. 2006, 45, 4796-4798;
30. o) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 6903-6907;
31. Angew. Chem. Int. Ed. 2006, 45, 6751-6755;
32. p) M. Rueping, C. Azap, Angew. Chem. 2006, 118, 7996-7999;
33. Angew. Chem. Int. Ed. 2006, 45, 7832-7835;
34. q) M. Terada, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 292-293;
35. r) G. Li, Y. Liang, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 5830-5831;
36. s) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756-6764;
37. t) J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498-7499;
38. u) M. Terada, K. Machioka, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 10336-10337;
39. v) S. C. Pan, J. Zhou, B. List, Angew. Chem. 2007, 119, 618-620;
40. Angew. Chem. Int. Ed. 2007, 46, 612-614;
41. w) M. Rueping, A. P. Antonchick, Angew. Chem. 2007, 119, 4646-4649;
42. Angew. Chem. Int. Ed. 2007, 46, 4562-4565.
43. D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626-9627.
44. M. Rueping, W. Ieawsuwan, A. P. Antonchick, B. J. Nachtsheim, Angew. Chem. 2007, 119, 2143-2146;
45. Angew. Chem. Int. Ed. 2007, 46, 2097-2100.
46. A. Wittkopp, P. R. Schreiner, Chem. Eur. J. 2003, 9, 407-414.
47. K. B. Simonsen, P. Bayon, R. G. Hazell, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 1999, 121, 3845-3853.
48. III complex catalyzed endo selective 1,3-dipolar cycloaddition of dihydrofuran with nitrones, see: T. Ashizawa, N. Ohtsuki, T. Miura, M. Ohya, T. Shinozaki, T. Ikeno, T. Yamada, Heterocycles 2006, 68, 1801-1810.
49. For optimization of reaction conditions, see the Supporting Information.
50. F. Belaj, Acta Crystallogr. Sect. B 1993, 49, 254-258.
51. a) K. V. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 1996, 61, 346-355;
52. b) K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-909.
53. a) S. E. Denmark, M. Seierstad, B. Herbert, J. Org. Chem. 1999, 64, 884-901;
54. b) K. V. Gothelf, K. A. Jørgensen, Chem. Commun. 2000, 1449-1458;
55. c) G. Desimoni, G. Faita, M. Mella, M. Boiocchi, Eur. J. Org. Chem. 2005, 1020-1027.
56. D. Nakashima, H. Yamamoto, Org. Lett. 2005, 7, 1251-1253.