Vinylogous Mannich-type reaction catalyzed by an iodine-substituted chiral phosphoric acid

Advanced Synthesis and Catalysis

Volumn 350, Issue 3, 2008, Pages 399-402

  Akiyama, Takahiko ^a   Honma, Yasuhiro ^a   Itoh, Junji ^a   Fuchibe, Kohei ^a,b  

^a GAKUSHUIN UNIVERSITY   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Addition to imines; Amines; Asymmetric catalysis; Asymmetric synthesis; C C bond formation; Organic catalysis

Indexed keywords

EID: 53549088683     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700521     Document Type: Article

References (53)

1. a) N. B. Carter, A. E. Nadany, J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1 2002, 2324;
2. b) H. M. C. Ferraz, L. S. Longo, M. V. A. Grazini, Synthesis 2002, 2155.
3. a) S. P. Brown, N. C. Goodwin, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 1192;
4. b) K. Kong, D. Romo, Org. Lett. 2006, 8, 2909.
5. a) T. Tsukamoto, T. Kitazume, Chem. Lett. 1992, 1377;
6. b) G. Rassu, L. Pinna, P. Spanu, N. Culeddu, G. Casiraghi, Tetrahedron 1992, 48, 727;
7. c) G. Casiraghi, G. Rassu, P. Spanu, L. Pinna, F. Ulgheri, J. Org. Chem. 1993, 58, 3397;
8. d) G. Casiraghi, G. Rassu, Synthesis 1995, 607;
9. e) L. Battistini, F. Zanardi, G. Rassu, P. Spanu, G. Pelosi, G. Fava, M. B. Ferrari, G. Casiraghi, Tetrahedron: Asymmetry 1997, 8, 2975;
10. f) S. F. Martin, O. D. Lopez, Tetrahedron Lett. 1999, 40, 8949;
11. g) L. Battistini, G. Rassu, L. Pinna, F. Zanardi, G. Casiraghi, Tetrahedron: Asymmetry 1999, 10, 765;
12. h) M. V. Spanedda, M. Ourévitch, B. Benoit, J.-P. Bégué, D. Bonnet-Delpon, Tetrahedron Lett. 2004, 45, 5023;
13. i) S. Oudeyer, B. Dudot, J. Rorer, Heterocycles 2005, 65, 823.
14. For a review, see: S. F. Martin, Acc. Chem. Res. 2005, 38, 895.
15. E. L. Carswell, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2006, 118, 7388;
16. Angew. Chem. Int. Ed. 2006, 45, 7230.
17. T.-Y. Liu, H.-L. Cui, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, J. Am. Chem. Soc. 2007, 129, 1878;
18. B. Niess, K. A. Jørgensen, Chem. Commun. 2007, 1620.
19. For reviews on chiral Brønsted acid catalysis, see: a) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289;
20. b) P. M. Pihko, Angew. Chem. 2004, 116, 2110;
21. Angew. Chem. Int. Ed. 2004, 43, 2062;
22. c) C. Bolm, T. Rantanen, I. Schiffers, L. Zani, Angew. Chem. 2005, 117, 1788;
23. Angew. Chem. Int. Ed. 2005, 44, 1758;
24. d) Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299;
25. e) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550;
26. Angew. Chem. Int. Ed. 2006, 45, 1520;
27. f) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999.
28. a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592;
29. Angew. Chem. Int. Ed. 2004, 43, 1566;
30. b) T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, Org. Lett. 2005, 7, 2583;
31. c) T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe, Adv. Synth. Catal. 2005, 347, 1523;
32. d) T. Akiyama, Y. Tamura, J. Itoh, H. Morita, K. Fuchibe, Synlett 2006, 141;
33. e) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. 2006, 118, 4914;
34. Angew. Chem. Int. Ed. 2006, 45, 4796;
35. f) T. Akiyama, H. Morita, K. Fuchibe, J. Am. Chem. Soc. 2006, 128, 13070;
36. g) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756.
37. For selected examples, see: a) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356;
38. b) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696;
39. c) M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781;
40. d) S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590;
41. Angew. Chem. Int. Ed. 2005, 44, 7424;
42. e) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84;
43. f) D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626;
44. g) X.-H. Chen, X.-Y. Xu, H. Liu, L.-F. Cun, L.-Z. Gong, J. Am. Chem. Soc. 2006, 128. 14802;
45. h) Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484;
46. i) M. J. Wanner, R. N. S. v. d. Haas, K. R. d. Cuba, J. H. v. Maarseveen, H. Hiemstra, Angew. Chem. 2007, 119, 7629;
47. Angew. Chem. Int. Ed. 2007, 46, 7485.
48. For reviews on chiral phosphoric acid catalysis, see: a) S. J. Connon, Angew. Chem. 2006, 118, 4013;
49. Angew. Chem. Int. Ed. 2006, 45, 3909;
50. b) T. Akiyama, Chem. Rev. 2007, 107, 5744.
51. For a chiral phosphoric acid catalyzed aza Friedel-Crafts reaction of methoxyfuran with aldimines, see: D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804.
52. CCDC 665887 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the Internet at www.ccdc.cam.uk/data_request/cif (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
53. Wavefunction, Inc. (Irvine, CA, USA).