An unexpected organocatalytic asymmetric tandem Michael/Morita-Baylis- Hillman reaction

Angewandte Chemie - International Edition

Volumn 47, Issue 1, 2008, Pages 121-125

  Cabrera, Silvia ^a   Alemán, José ^a   Bolze, Patrick ^a   Bertelsen, Søren ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Aldehydes; Amines; Nazarov reagent; Organocatalysis; Tandem reactions

Indexed keywords

AMINES; CATALYST ACTIVITY;

NAZAROV REAGENT; ORGANOCATALYSIS; TANDEM REACTIONS;

ALDEHYDES;

EID: 37549037472     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704076     Document Type: Article

References (94)

1. For recent reviews on organocatalysis, see for example: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
2. Angew. Chem. Int. Ed. 2004, 43, 5138;
3. b) A. Berkessel, H. Gröger, Asymmetric Organocatalysis, VCH, Weinheim, Germany, 2004;
4. c) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719;
5. d) Acc. Chem. Res. 2004, 37(8), special issue on organocatalysis;
6. e) B. List, J.-W. Yang, Science 2006, 313, 1584;
7. f) M. J. Gaunt, C. C. C. Johansson, A. McNally, N. C. Vo, Drug Discovery Today 2007, 12, 8;
8. g) B. List, Chem. Commun. 2006, 819;
9. h) P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007;
10. for general reviews of β funtionalization, see i) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701;
11. j) D. Almaşi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299.
12. For a definition and classification of one-pot reactions, see a) D. E. Fogg, E. N. dos Santos, Coord. Chem. Rev. 2004, 248, 2365;
13. b) C. J. Chapman, C. G. Frost, Synthesis 2007, 1.
14. For recent general reviews on domino, multicomponent reactions, see for example: a) J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001 ;
15. b) D. J. Ramon, M. Yus, Angew. Chem. 2005, 117, 1628;
16. Angew. Chem. Int. Ed. 2005, 44, 1602;
17. c) J. Zhu, H. Bienaymé, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005;
18. d) L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006;
19. e) H.-C. Guo, J.-A. Ma, Angew. Chem. 2006, 118, 362;
20. Angew. Chem. Int. Ed. 2006, 45, 354;
21. f) H. Pellissier, Tetrahedron 2006, 62, 362;
22. g) H. Pellissier, Tetrahedron 2006, 62, 2143.
23. For recent examples of enamine organocatalyzed reactions, see for example: a) M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001;
24. b) G. Guillena, D. J. Ramón, Tetrahedron: Asymmetry 2006, 17, 1465;
25. c) N. Mase, K. Watanabe, H. Yoda, K. Tanabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966;
26. d) S. Samanta, C.-G. Zhao, J. Am. Chem. Soc. 2006, 128, 7442;
27. e) Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. 2006, 118, 972;
28. Angew. Chem. Int. Ed. 2006, 45, 958;
29. f) T. Kano, M. Ueda, J. Takai, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 6046;
30. g) J. Alemán, S. Cabrera, E. Maerten, J. Overgaard, K. A. Jørgensen, Angew. Chem. 2007, 119, 5616;
31. Angew. Chem. Int. Ed. 2007, 46, 5520;
32. h) M. Tiecco, A. Carlone, S. Sternativo, F. Marini, G. Bartoli, P. Melchiorre, Angew. Chem. 2007, 119, 7006;
33. Angew. Chem. Int. Ed. 2007, 46, 6882.
34. For recent examples of iminium activation, see for example: a) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299;
35. Angew. Chem. Int. Ed. 2006, 45, 4193;
36. b) S. Brandau, A. Landa, J. Franzén, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411;
37. Angew. Chem. Int. Ed. 2006, 45, 4305;
38. c) H. Gotoh, R. Masui, H. Ogino, M. Shoji, Y. Hayashi, Angew. Chem. 2006, 118, 7007;
39. Angew. Chem. Int. Ed. 2006, 45, 6853;
40. d) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354;
41. e) Y. K. Chen, M. Yoshida, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328;
42. f) S. Bertelsen, P. Dinér, R. L. Johansen, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 1536;
43. g) P. Dinér, M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 2029;
44. Angew. Chem. Int. Ed. 2007, 46, 1983;
45. h) D. Enders, M. H. Bonten, G. Raabe, Synlett 2007, 6, 885;
46. i) A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588;
47. Angew. Chem. Int. Ed. 2007, 46, 4504;
48. j) I. Ibrahem, R. Rios, J. Vesely, P. Hammar, L. Erikson, F. Himo, A. Córdova, Angew. Chem. 2007, 119, 4591;
49. Angew. Chem. Int. Ed. 2007, 46, 4507.
50. For a review on organocatalytic domino reactions, see a) D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590;
51. Angew. Chem. Int. Ed. 2007, 46, 1570, and references therein;
52. for selected recent publications, see b) S. Brandau, E. Maerten, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 14986;
53. c) H. Sundén, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Chem. Eur. J. 2007, 13, 574;
54. d) H. Sundén, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Adv. Synth. Catal. 2007, 349, 827;
55. e) A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119;
56. Angew. Chem. Int. Ed. 2007, 46, 1101;
57. f) H. Li, L. Zu, H. Xie, J. Wang, W. Jiang, W. Wang, Org. Lett. 2007, 9, 1833;
58. g) J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498;
59. h) D. Enders, A. A. Narine, T. R. Benninghaus, G. Raabe, Synlett 2007, 1667;
60. i) R. Rios, J. Vesely, H. Sundéh, I. Ibrahem, G.-L. Zhao, A. Córdova, Tetrahedron Lett. 2007, 48, 5835;
61. j) Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010;
62. Angew. Chem. Int. Ed. 2007, 46, 4922;
63. k) H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886.
64. a) D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861;
65. b) D. Enders, M. R. M. Hüttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. 2007, 119, 471;
66. Angew. Chem. Int. Ed. 2007, 46, 467.
67. For recent reviews on the Morita-Baylis-Hillman reaction, see a) G. Masson, C. Housseman, J. Zhu, Angew. Chem. 2007, 119, 4698;
68. Angew. Chem. Int. Ed. 2007, 46, 4614;
69. b) Y.-L. Shi, M. Shi, Eur. J. Org. Chem. 2007, 2905;
70. c) D. Basavaiah, K. V. Rao, R. J. Reddy, Chem. Soc. Rev. 2007, 36, 1581.
71. a) J. E. Imbriglio, M. M. Vasbinder, S. J. Miller, Org. Lett. 2003, 5, 3741;
72. b) S. H. Chen, B. C. Hong, C. F. Su, S. Sarshar, Tetrahedron Lett. 2005, 46, 8899;
73. c) C. E. Aroyan, M. M. Vasbinder, S. J. Miller, Org. Lett. 2005, 7, 3849;
74. d) A. Nakano, S. Kawahara, S. Akamatsu, K. Morokuma, M. Nakatani, Y. Iwabuchi, K. Takahashi, J. Ishihara, S. Hatekeyama, Tetrahedron 2006, 62, 381;
75. e) M. M. Vasbinder, J. E. Imbriglio, S. J. Miller, Tetrahedron 2006, 62, 11450;
76. for two examples on aza-Morita-Baylis-Hillman-type products, see f) N. Utsumi, H. Zhang, F. Tanaka, C. F. Barbas III, Angew. Chem. 2007, 119, 1910;
77. Angew. Chem. Int. Ed. 2007, 46, 1878;
78. g) J. Vesely, P. Dziedzic, A. Córdova, Tetrahedron Lett. 2007, 48, 6900.
79. R. Zibuch, J. Streiber, Organic Syntheses Coll. Vol. 9, 1998, p. 432;
80. Vol. 71, 1993, p. 236.
81. For the first application of silyldiarylprolinol ethers as catalysts, see a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804;
82. Angew. Chem. Int. Ed. 2005, 44, 794,
83. see also b) M. Marigo, D. Fielenbach, A. Braunton, A. Kjærsgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769;
84. Angew. Chem. Int. Ed. 2005, 44, 3703;
85. c) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
86. Angew. Chem. Int. Ed. 2005, 44, 4212;
87. d) J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 18296;
88. e) C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042;
89. Angew. Chem. Int. Ed. 2006, 45, 7876.
90. 1H NMR spectroscopic analysis of the crude mixture showed a 90% conversion with a 7:1 ratio of the intermediate 6 to the tandem product 4a.
91. M. D. Burke, S. L. Schreiber, Angew. Chem. 2004, 116, 48;
92. Angew. Chem. Int. Ed. 2004, 43, 46.
93. CCDC-661574 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..
94. For more details about the determination of the absolute configuration of all the compounds, see the Supporting Information.