Thermal effects in the organocatalytic asymmetric α-amination of disubstituted aldehydes with azodicarboxylates: A high-temperature organocatalysis

European Journal of Organic Chemistry

Volumn , Issue 13, 2008, Pages 2207-2212

  Baumann, Thomas ^a   Bächle, Michael ^a   Hartmann, Caroline ^a   Bräse, Stefan ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

amination; Amino aldehydes; Microwave; Organocatalysis

Indexed keywords

EID: 53749097933     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701167     Document Type: Article

References (75)

1. D. H. R. Barton, W. D. Ollis, Comprehensive Organic Chemistry, vol. 5, Pergamon Press, Oxford, 1979, part 22, p. 21; part 23, p. 177; part 28, p. 867; part 30, p. 1043.
2. a) A. Ricci, Modern Amination Methods, Wiley-VCH, 2000;
3. b) J. Mulzer, H. J. Altenbach, M. Braun, K. Krohn, H. U. Reissig, Organic Synthesis Highlights, VCH Publishers, Weinheim, 1991, p. 45.
4. Review: c) E. Erdik, M. Ay, Chem. Rev. 1989, 89, 1947.
5. See also: d) P. Gmeiner, B. Bollinger, Liebigs Ann. Chem. 1992, 273;
6. e) S. Andreae, E. Schmitz, Heterocycles 1994, 37, 379;
7. f) H. Mitchell, Y. Leblanc, J. Org. Chem. 1994, 59, 682.
8. Feature article: S. Bräse, T. Baumann, S. Dahmen, H. Vogt, Chem. Commun. 2007, 1881.
9. For chiral organometallic reagents, see: a) D. K. An, K. Hirakawa, S. Okamoto, F. Sato, Tetrahedron Lett. 1999, 40, 3737;
10. b) R. W. Hoffmann, B. Hölzer, O. Knopff, Org. Lett. 2001, 3, 1945.
11. For chiral phosphorus-stabilized anions, see: c) S. E. Denmark, N. Chatani, S. V. Pansare, Tetrahedron 1992, 48, 2191;
12. d) G. Jommi, G. Miglierini, R. Pagliarin, G. Sello, M. Sisti, Tetrahedron 1992, 48, 7275;
13. e) S. Hanessian, Y. L. Bennani, Synthesis 1994, 1272;
14. f) R. Pagliarin, G. Papeo, G. Sello, M. Sisti, L. Paleari, Tetrahedron 1996, 52, 13783.
15. B. List, J. Am. Chem. Soc. 2002, 124, 5656.
16. a) A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. Int. Ed. 2002, 41, 1790.
17. Reviews: b) R. O. Duthaler, Angew. Chem. Int. Ed. 2003, 42, 975;
18. c) J. M. Janey, Angew. Chem. Int. Ed. 2005, 44, 4292;
19. d) C. Greck, B. Drouillat, C. Thomassigny, Eur. J. Org. Chem. 2004, 1377.
20. a) B. List, A. R. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395;
21. b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386;
22. c) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573;
23. d) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475;
24. e) C. Pidathala, L. Hoang, N. Vignola, B. List, Angew. Chem. Int. Ed. 2003, 42, 2785.
25. a) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798;
26. b) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620;
27. c) N. S. Chowdari, D. B. Ramachary, A. Cordova, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591;
28. d) A. Cordova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301;
29. e) A. Cordova, W. Notz, C. F. Barbas III, Chem. Commun. 2002, 3024;
30. f) Y. Sekiguchi, A. Sasaoka, A. Shimomoto, S. Fujioka, H. Kotsuki, Synlett 2003, 1655;
31. g) A. Bøgevig, T. B. Poulsen, W. Zhuang, K. A. Jørgensen, Synlett 2003, 1915.
32. a) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
33. b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827;
34. c) Y. Hayashi, W. Tsuboi, M. Shoji, N. Suzuki, J. Am. Chem. Soc. 2003, 125, 11208;
35. d) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. Int. Ed. 2003, 42, 3677;
36. e) A. Cordova, Synlett 2003, 1651;
37. f) W. Notz, F. Tanaka, S. Watanabe, N. S. Chaudari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624.
38. a) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423;
39. b) D. Enders, A. Seki, Synlett 2002, 26.
40. N. Vignola, B. List, J. Am. Chem. Soc. 2004, 126, 450.
41. a) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808;
42. b) G. Zhong, Angew. Chem. Int. Ed. 2003, 42, 4247;
43. c) Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Tetrahedron Lett. 2003, 44, 8293.
44. a) Y. Hayashi, J. Yamaguchi, T. Sumiya, M. Shoji, Angew. Chem. Int. Ed. 2004, 43, 1112;
45. b) A. Bøgevig, H. Sundéen, A. Cordova, Angew. Chem. Int. Ed. 2004, 43, 1109.
46. M. P. Brochu, S. P. Brown, D. W. C. Macmillan, J. Am. Chem. Soc. 2004, 126, 4108.
47. N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790.
48. a) H. Vogt, S. Vanderheiden, S. Bräse, Chem. Commun. 2003, 2448;
49. b) T. Baumann, H. Vogt, S. Bräse, Eur. J. Org. Chem. 2007, 266.
50. a) T. Baumann, M. Bächle, S. Bräse, Org. Lett. 2006, 8, 3797;
51. b) see also: H. Vogt, T. Baumann, M. Nieger, S. Bräse, Eur. J. Org. Chem. 2006, 5815.
52. B. Rodriguez, C. Bolm, J. Org. Chem. 2006, 71, 2888.
53. S. Mosse, A. Alexakis, Org. Lett. 2006, 8, 3577.
54. B. L. Hayes, Microwave Synthesis, CEM publishing, 2002.
55. max = 40°C) of the instrument. Thus, at the present stage, a reliable error margin of the given temperatures (Tables 1-4) cannot be given. This should, however, not affect the reproducibility of the experiments. For a comparative study of temperature determinations under MW irradiations, see: M. N. B. Ondruschka, D. Weiß, R. Beckert, W. Bonrath, A. Gum, Chem. Eng. Technol. 2005, 28, 871.
56. C. O. Kappe, Angew. Chem. Int. Ed. 2004, 43, 6250 and cited references therein.
57. a) A. J. A. Cobb, D. M. Shaw, S. V. Ley, Synlett 2004, 558;
58. b) H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. Int. Ed. 2004, 43, 1983;
59. c) A. Hartikka, P. I. Arvidsson, Tetrahedron: Asymmetry 2004, 15, 1831;
60. d) A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84.
61. Reviews: a) G. Lelais, D. W. C. MacMillan, Aldrichim. Acta 2006, 39, 79;
62. b) M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001;
63. c) E. Diez, S. V. Ley, Chemtracts 2000, 13, 592;
64. d) K. Takasu, S. Maiti, M. Ihara, Heterocycles 2003, 59, 51;
65. e) M. Bandini, M. Fagioli, P. Melchiorre, A. Melloni, A. Umani-Ronchi, Tetrahedron Lett. 2003, 44, 5843;
66. f) M. T. Hechavarria Fonseca, B. List, Angew. Chem. Int. Ed. 2004, 43, 3958.
67. 3).
68. a) D. J. Bailey, D. O'Hagan, M. Tavasli, Tetrahedron: Asymmetry 1997, 8, 149;
69. b) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 695;
70. c) E. Sipos, A. Tungler, I. J. Bitter, Mol. Catal. A Chem. 2003, 198, 167;
71. d) P. Melchiorre, K. A. Jørgensen, J. Org. Chem. 2003, 68, 4151;
72. e) K. Kuhl, K. A. Jørgensen, Angew. Chem. Int. Ed. 2003, 42, 1498;
73. f) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. Int. Ed. 2005, 44, 794;
74. g) S. Bertelsen, N. Halland, S. Bachmann, M. Marigo, A. Braunton, K. A. Jørgensen, Chem. Commun. 2005, 38, 4821.
75. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.