Direct catalytic enantioselective aza-Diels-Alder reactions

Angewandte Chemie - International Edition

Volumn 44, Issue 31, 2005, Pages 4877-4880

  Sundén, Henrik ^a   Ibrahem, Ismail ^a   Eriksson, Lars ^a   Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Asymmetric catalysis; Bicyclic amino acids; Cycloaddition; Enantioselectivity; Ketones

Indexed keywords

AMINES; AMINO ACIDS; DERIVATIVES; FORMALDEHYDE; KETONES; REACTION KINETICS; UNSATURATED COMPOUNDS;

ASYMMETRIC CATALYSIS; BICYCLIC AMINO ACIDS; CYCLOADDITION; ENANTIOSELECTIVITY;

CATALYSIS;

AMINE; IMINE; KETONE; PROLINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; IMINES; KETONES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROLINE; STEREOISOMERISM;

EID: 23744473863     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500811     Document Type: Article

References (70)

1. For reviews, see a) K. A. Jørgensen, Angew. Chem. 2000, 112, 3702;
2. Angew. Chem. Int. Ed. 2000, 39, 3558;
3. b) D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic-Syntehsis, Academic Press, San Diego. 1987, chap. 2;
4. c) H. Waldmann, Synlett 1995, 133;
5. d) L. F. Tietze, G. Kettschau, Top. Curr. Chem. 1997, 190, 1;
6. e) S. M. Weinreb, Top. Curr. Chem. 1997, 190, 131;
7. f) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069.
8. For examples of synthesis of complex compounds by an aza-Diels-Alder reaction, see a) R. T. Bailey, R. S. Garigipati, J. A. Morton, S. M. Weinreb, J. Am. Chem. Soc. 1984, 106, 3240;
9. b) R. Lock, H. Waldmann, Liebgs. Ann. Chem. 1994, 511;
10. c) A. B. Holmes, A. Kee, T. Ladduwahetty, D. F. Smith, J. Chem. Soc. Chem. Commun. 1990, 1412.
11. For examples of diastereoselective aza-Diels-Alder reactions, see a) J. Barluenga, F. Aznar, C. Valdéz, A. Martín, S. García- Granada, E. Martín, J. Am. Chem. Soc. 1993, 115, 4403;
12. b) A. S. Timen, A. Ficher, P. Somfai, Chem. Commun. 2003, 1150;
13. c) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1445;
14. Angew. Chem. Int. Ed. Engl. 1990, 29, 1468;
15. d) S. D. Larsen, P. A. Grieco, J. Am. Chem. Soc. 1985, 107, 1768.
16. Stoichiometric amounts of chiral boron complexes have also been used to mediate enantiosalective aza-Diels-Alder reactions, see a) K. Hattori, H. Yamamoto, J. Org. Chem. 1992, 57, 3264;
17. b) K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10520.
18. a) H. Ishitani, S. Kobayashi, Tetrahedron Lett. 1996, 37, 7357;
19. b) S. Kobayashi, S. Komiyama, H. Ishitani, Angew. Chem. 1998, 110, 1026;
20. Angew. Chem. Int. Ed. 1998, 37, 979;
21. c) S. Kobayashi, K. Kusakabe, S. Komiyama, H. Ishitani, J. Org. Chem. 1999, 64, 4220.
22. a) S. Yao, M. Johannsen, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 1998, 110, 3318;
23. Angew. Chem. Int. Ed. 1998, 37, 3121;
24. b) S. Yao, S. Saaby, R. G. Hazell, K. A. Jørgensen, Chem. Eur. J. 2000, 6, 2435.
25. see also: a) N. S. Josephsohn, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 4018;
26. b) O. G. Mancheño, R. G. Arrayás, J. C. Carretero, J. Am. Chem. Soc. 2004, 126, 456.
27. a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840;
28. Angew. Chem. Int. Ed. 2001, 40, 3726;
29. b) B. List, Tetrahedron 2002, 58, 5573;
30. c) R. O. Duthaler, Angew. Chem. 2003, 115, 1005;
31. Angew. Chem. Int. Ed. 2003, 42, 975;
32. d) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
33. Angew. Chem. Int. Ed. 2004, 43, 5138.
34. For organocatalytic Diels-Alder reactions, see a) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458;
35. b) K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
36. c) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Angew. Chem. 2003, 115, 4365;
37. Angew. Chem. Int. Ed. 2003, 42, 4233.
38. For reverse-electron-demand Diels-Alder reaction, see a) K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536;
39. Angew. Chem. Int. Ed. 2003, 42, 1498.
40. For hetero-Diels-Alder reactions, see a) Y. Huang, K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146;
41. b) K. A. Unni, N. Tanaka, H. Yamamoto, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 1336.
42. For nitroso-Diels-Alder reactions, see a) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962;
43. b) Y. Hayashi, J. Yamaguchi, K. Hibino, T. Sumiya, T. Urushima, M. Shoji, D. Hashizume, H. Koshino, Adv. Synth. Catal. 2004, 346, 1435;
44. c) H. Sundén, N. Dahlin, I. Ibrahem, H. Adolfsson, A. Córdova, Tetrahedron Lett. 2005, 46, 3385.
45. For 1,3-dipolar cycloadditions, see a) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874;
46. b) S. Karlsson, H. Högberg, Tetrahedron: Asymmetry 2002, 13, 923;
47. for [4+3] cycloadditions , see c) M. Harmata, S. K. Ghosh, X. Hong, S. Wacharasindhu, P. Kirchhoefer, J. Am. Chem. Soc. 2003, 125, 2058.
48. a) J. Casas, M. Engqvist, I. Ibrahem, B. Kaynak, A. Córdova, Angew. Chem. 2005, 117, 1367;
49. Angew. Chem. Int. Ed. 2005, 44, 1343;
50. b) A. Córdova, H. Sundén, M. Engqvist, I. Ibrahem, J. Casas, J. Am. Chem. Soc. 2004, 126, 8914;
51. c) H. Sundén, M. Engqvist, J. Casas, I. Ibrahem, A. Córdova, Angew. Chem. 2004, 116, 6694;
52. Angew. Chem. Int. Ed. 2004, 43, 6532;
53. d) A. Córdova, Acc. Chem. Res. 2004, 37, 102;
54. e) A. Bøgevig, H, Sundén, A. Córdova, Angew. Chem. 2004, 116, 1129;
55. Angew. Chem. Int. Ed. 2004, 43, 1109;
56. f) A. Córdova, H. Sundén, A. Bøgevig, M. Johansson, F. Himo, Chem. Eur. J. 2004, 10, 3673;
57. g) A. Córdova, Chem. Eur. J. 2004, 10, 1987;
58. h) A. Córdova, Synlett 2003, 1651, and references therein.
59. This strategy has been used successfully in a direct catalytic one-pot three-component Mannich reaction, see a) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
60. b) B. List, P. Porjaliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827;
61. c) I. Ibrahem, J. Casas, A. Córdova, Angew. Chem. 2004, 116, 6690;
62. Angew. Chem. Int. Ed. 2004, 43, 6528, and references therein.
63. The aza-Diels-Alder products decomposed and underwent a retro-Michael reaction upon chromatography on silica gel, which decreased the yield.
64. For the first use of catalyst 4, see a) A. J. A. Cobb, D. M. Shaw, S. V. Ley, Synlett 2004, 558;
65. b) H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. 2004, 116, 2017;
66. Angew. Chem. Int. Ed. 2004, 43, 1983;
67. c) A. Hartikaa, P. I. Arvidsson, Tetrahedron: Asymmetry 2004, 15, 1831.
68. Arylsulfonylcarboxamides have been used in aldol reactions, see a) A. Berkessel, B. Koch, J. Lex, Adv. Synth. Catal. 2004, 346, 1141; for the use of catalyst 5, see reference [12c]
69. and b) A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84.
70. CCDC-265109 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.