Chiral Brøsted acids in the catalytic asymmetric nazarov cyclization - The first enantioselective organocatalytic electrocyclic reaction

Angewandte Chemie - International Edition

Volumn 46, Issue 12, 2007, Pages 2097-2100

  Rueping, Magnus ^a   Ieawsuwan, Winai ^a   Antonchick, Audrey P ^a   Nachtsheim, Boris J ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

Binol phosphate; Br nsted acids; Electrocyclization; Ion pair catalysis; Nazarov cyclization

Indexed keywords

CATALYSIS; CYCLIZATION; ENANTIOSELECTIVITY; SYNTHESIS (CHEMICAL);

BRANSTED ACID; DIASTEREOMERS; ION-PAIR CATALYSIS;

ORGANIC ACIDS;

EID: 34250725648     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604809     Document Type: Article

References (62)

1. Reviews: a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289;
2. b) P. M. Pihko, Angew. Chem. 2004, 116, 2110;
3. Angew. Chem. Int. Ed. 2004, 43, 2062;
4. c) C. Bolm, T. Rantanen, I. Schiffers, L. Zani, Angew. Chem. 2005, 117, 1788;
5. Angew. Chem. Int. Ed. 2005, 44, 1758;
6. d) H. Yamamoto, K. Futatsugi, Angew. Chem. 2005, 117, 1958;
7. Angew. Chem. Int. Ed. 2005, 44, 1924;
8. e) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550;
9. Angew. Chem. Int. Ed. 2006, 45, 1520;
10. f) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999.
11. a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592;
12. Angew. Chem. Int. Ed. 2004, 43, 1566;
13. b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
14. c) D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11 804;
15. d) T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, Org. Lett. 2005, 7, 2583;
16. e) T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe, Adv. Synth. Catal. 2005, 347, 1523;
17. f) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15 696;
18. g) M. Terada, K. Sorimachi, D. Uraguchi, Synlett 2006, 13;
19. h) S. Hofmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590;
20. Angew. Chem. Int. Ed. 2005, 44, 7424;
21. i) T. Akiyama, Y. Tamura, J. Itoh, H. Morita, K. Fuchibe, Synlett 2006, 141;
22. j) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84;
23. k) J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1087;
24. l) M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2006, 118, 2312;
25. Angew. Chem. Int. Ed. 2006, 45, 2254;
26. m) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299;
27. Angew. Chem. Int. Ed. 2006, 45, 4193;
28. n) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914;
29. Angew. Chem. Int. Ed. 2006, 45, 4796;
30. o) A. Hasegawa, Y. Naganawa, M. Fushimi, K. Ishihara, H. Yamamoto, Org. Lett. 2006, 8, 3175;
31. p) S. Hoffmann, M. Nicoletti, B. List, J. Am. Chem. Soc. 2006, 128, 13 074;
32. q) N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13 368;
33. r) T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13 070;
34. s) application of triflyl phosphoramides: D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626.
35. a) M. Rueping, C. Azap, E. Sugiono, T. Theissmann, Synlett 2005, 2367;
36. b) M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781;
37. c) M. Rueping, A. P. Antonchick, T. Theissmann, Synlett 2006, 1071;
38. d) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765;
39. Angew. Chem. Int. Ed. 2006, 45, 3683;
40. e) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 6903;
41. Angew. Chem. Int. Ed. 2006, 45, 6751.
42. a) M. Rueping, E. Sugiono, C. Azap, Angew. Chem. 2006, 118, 2679;
43. Angew. Chem. Int. Ed. 2006, 45, 2617;
44. b) M. Rueping, E. Sugiono, S. A. Moreth, Adv. Synth. Catal. 2007, 349, in press.
45. M. Rueping, C. Azap, Angew. Chem. 2006, 118, 7996;
46. Angew. Chem. Int. Ed. 2006, 45, 7832.
47. Reviews on the Nazarov cyclization: a) K. L. Habermas, S. E. Denmark, T. K. Jones, Org. React. 1994, 45, 1-158;
48. b) S. E. Denmark in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Flemming), Pergamon, Oxford, 1991, p. 51;
49. c) A. J. Frontier, C. Collison, Tetrahedron 2005, 61, 7577;
50. d) H. Pellissier, Tetrahedron 2005, 61, 6479;
51. e) M. A. Tius, Eur. J. Org. Chem. 2005, 2193.
52. Metal-catalyzed enantioselective Nazarov reactions: a) G Liang, S. N. Gradl, D. Trauner, Org. Lett. 2003, 5, 5931;
53. b) V. K. Aggarwal, A. J. Belfield, Org. Lett. 2003, 5, 5075;
54. asymmetric Nazarov reactions through enantioselective protonations: c) G. Liang, D. Trauner, J. Am. Chem. Soc. 2004, 126, 9544.
55. Dienones 2-12 have been chosen on the basis of the favored s-trans/s-trans orientation and the stabilization of the oxyallyl cation formed as an intermediate.
56. The N-triflyl phophoramides 1f and 1g were prepared by a slightly modified procedure of Nakashima and Yamamoto (Ref. [2s]).
57. Examples of Nazarov reactions with low catalyst loadings: a) T. K. Jones, S. E. Denmark, Helv. Chim. Acta 1983, 66, 2377;
58. b) S. Giese, F. G. West, Tetrahedron 2000, 56, 10 221;
59. c) W. He, J. F. Sun, A. J. Frontier, J. Am. Chem. Soc. 2003, 125, 14 278;
60. d) C. Bee, E. Leclerc, M. A. Tius, Org. Lett. 2003, 5, 4927;
61. e) M. Janka, W. He, A. J. Frontier, R. Eisenberg, J. Am. Chem. Soc. 2004, 126, 6846.
62. A comparison of catalysts 1f and 1g is given in the Supporting Information.