Asymmetric michael reaction of acetaldehyde with nitroolefins catalyzed by highly water-compatible organocatalysts in aqueous media

Advanced Synthesis and Catalysis

Volumn 354, Issue 14-15, 2012, Pages 2849-2853

  Qiao, Yupu ^a   He, Junpeng ^a   Ni, Bukuo ^a   Headley, Allan D ^a  

^a TEXAS A AND M UNIVERSITY COMMERCE   (United States)

Author keywords

Acetaldehyde; Asymmetric synthesis; Michael reaction; water compatible organocatalysts

Indexed keywords

EID: 84869029038     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200215     Document Type: Article

References (121)

1. For recent reviews see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
2. Angew. Chem. Int. Ed. 2004, 43, 5138;
3. b) G. Guillena, D. J. Ramon, Tetrahedron: Asymmetry 2006, 17, 1465;
4. c) B. List, Chem. Commun. 2006, 819;
5. d) G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79;
6. e) M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001;
7. f) J. L. Vicario, D. Badia, L. Carrillo, Synthesis 2007, 2065;
8. g) H. Pellissier, Tetrahedron 2007, 63, 9267;
9. h) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
10. Angew. Chem. Int. Ed. 2008, 47, 4638;
11. i) M. Gruttadauria, F. Giacalone, R. Noto, Chem. Soc. Rev. 2008, 37, 1666;
12. j) D. A. Longbottom, V. Franckevicius, S. Kumarn, A. J. Oelke, V. Wascholowski, S. V. Ley, Aldrichimica Acta 2008, 41, 3;
13. k) D. W. C. MacMillan, Nature 2008, 455, 304;
14. l) S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178;
15. m) E. N. Jacobsen, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2010, 107, 20618.
16. Special issues on organocatalysis: n) Chem. Rev. 2007, 107, 5413;
17. o) Acc. Chem. Res. 2004, 37, 631;
18. p) Adv. Synth. Catal. 2004, 346, 1007;
19. q) Tetrahedron 2006, 62, 243.
20. Recent books see: r) A. Berkessel, H. Grçger, (Eds.), Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2005;
21. s) P. I. Dalko, (Ed.), Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007;
22. t) I. McCort-Tranchepain, M. Petit, P. I. Dalko, Handbook of Green Chemistry: Organocatalysis, Wiley-VCH, Weinheim, 2009;
23. u) A. J. B. Watson, D. W. C. MacMillan, Catalytic Asymmetric Synthesis: Enantioselective Organocatalysis Involving Iminium, Enamine, Somo, and Photoredox Activation, 3rd edn., Wiley-VCH, Weinheim, 2010;
24. v) Asymmetric Organocatalysis-Workbench Edition, (Eds.: B. List, K. Maruoka), Georg Thieme Verlag, Stuttgart, 2012.
25. For recent reviews, see: a) N. Krause, A. Hoffmann- Roder, Synthesis 2001, 171;
26. b) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877;
27. c) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701;
28. d) D. Almas, D. A. Alonso, C. Najera, Tetrahedron: Asymmetry 2007, 18, 299;
29. e) J. L. Vicario, D. Badia, L. Carrillo, Synthesis 2007, 14, 2065;
30. f) S.-M. Sarah, A. Alexandre, Chem. Commun. 2007, 3123;
31. g) Y. Zhang, W. Wang, Catal. Sci. Technol. 2012, 2, 42.
32. For reviews see: a) R. M. Figueiredo, M. Christmann, Eur. J. Org. Chem. 2007, 2575;
33. b) E. Marqués-López, R. P. Herrera, M. Christmann, Nat. Prod. Rep. 2010, 27, 1138;
34. c) C. Grondal, M. Jeanty, D. Enders, Nature Chemistry 2010, 2, 167.
35. For some selected examples, see: a) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423;
36. b) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737;
37. c) A. Alexakis, O. Andrey, Org. Lett. 2002, 4, 3611;
38. d) N. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 2527;
39. e) W. Wang, J. Wang, H. Li, Angew. Chem. 2005, 117, 1393;
40. Angew. Chem. Int. Ed. 2005, 44, 1369;
41. f) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
42. Angew. Chem. Int. Ed. 2005, 44, 4212;
43. g) C. Palomo, S. Vera, A. Mielgo, E. Gomez-Bengoa, Angew. Chem. 2006, 118, 6130;
44. Angew. Chem. Int. Ed. 2006, 45, 5984;
45. h) S. Mosse, A. Alexakis, Org. Lett. 2006, 8, 3577;
46. i) S. V. Pansare, K. Pandya, J. Am. Chem. Soc. 2006, 128, 9624;
47. j) M. P. Lalonde, Y. Chen, E. N. Jacobsen, Angew. Chem. 2006, 118, 6514;
48. Angew. Chem. Int. Ed. 2006, 45, 6366;
49. k) S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599;
50. l) M. T. Barros, A. M. F. Phillips, Eur. J. Org. Chem. 2007, 178;
51. m) S. Sulzer-Moss, A. Alexakis, Chem. Commun. 2007, 3123;
52. n) M. Wiesner, J. D. Revell, H. Wennemers, Angew. Chem. 2008, 120, 1897;
53. Angew. Chem. Int. Ed. 2008, 47, 1871;
54. o) A. Ma, S. Zhu, D. Ma, Tetrahedron Lett. 2008, 49, 3075;
55. p) C. Chang, S.-H. Li, R. J. Reddy, K. Chen, Adv. Synth. Catal. 2009, 351, 1273;
56. q) M. Wiesner, G. Upert, G. Angelici, H. Wennemers, J. Am. Chem. Soc. 2010, 132, 6;
57. r) R. Husmann, M. Jçrres, G. Raabe, C. Bolm, Chem. Eur. J. 2010, 16, 12549;
58. s) J.-R. Chen, Y.-Q. Zou, L. Fu, F. Ren, F. Tan, W.-J. Xiao, Tetrahedron 2010, 66, 5367;
59. t) W.-H. Wang, X.-B. Wang, K. Kodama, T. Hirose, G.- Y. Zhang, Tetrahedron 2010, 66, 4970;
60. u) F. Kelleher, S. Kelly, J. Watts, V. McKee, Tetrahedron 2010, 66, 3525.
61. For a review see: B. Alcaide, P. Almendros, Angew. Chem. 2008, 120, 4710;
62. Angew. Chem. Int. Ed. 2008, 47, 4632.
63. a) P. Garcia-Garcia, A. Ladepeche, R. Halder, B. List, Angew. Chem. 2008, 120, 4797;
64. Angew. Chem. Int. Ed. 2008, 47, 4719;
65. b) Y. Hayashi, T. Itoh, M. Ohkubo, H. Ishikawa, Angew. Chem. 2008, 120, 4800;
66. Angew. Chem. Int. Ed. 2008, 47, 4722.
67. a) K. I. Jentzsch, T. Min, J. I. Etcheson, J. C. Fettinger, A. K. Franz, J. Org. Chem. 2011, 76, 7065;
68. b) D. Enders, R. Krüll, W. Bettray, Synthesis 2010, 567;
69. c) S.- W. Wang, J. Chen, G.-H. Chen, Y.-G. Peng, Synlett 2009, 1457;
70. d) E. Alza, M. A. Pericàs, Adv. Synth. Catal. 2009, 351, 3051;
71. e) E. Zandvoort, E. M. Geertsema, B.-J. Baas, W. J. Quax, G. J. Poelarends, Angew. Chem. 2012, 124, 1266;
72. Angew. Chem. Int. Ed. 2012, 51, 1240.
73. For recent reviews about organocatalysis in aqueous media, see: a) A. P. Brogan, T. J. Dickerson, K. D. Janda, Angew. Chem. 2006, 118, 8278;
74. Angew. Chem. Int. Ed. 2006, 45, 8100;
75. b) Y. Hayashi, Angew. Chem. 2006, 118, 8281;
76. Angew. Chem. Int. Ed. 2006, 45, 8103;
77. c) M. Gruttadauria, F. Giacalone, R. Noto, Adv. Synth. Catal. 2009, 351, 33;
78. d) M. Raj, V. K. Singh, Chem. Commun. 2009, 6687;
79. e) N. Mase, C. F. Barbas III, Org. Biomol. Chem. 2010, 8, 4043;
80. f) Š. Toma, R. Šebesta, M. Mečiarová, Curr. Org. Chem. 2011, 15, 2257.
81. For some selected examples of aldol reactions in aqueous media, see: a) T. J. Dickerson, K. D. Janda, J. Am. Chem. Soc. 2002, 124, 3220;
82. b) H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. 2004, 116, 2017;
83. Angew. Chem. Int. Ed. 2004, 43, 1983;
84. c) Y. Hayashi, S. Aratake, T. Okano, J. Takahashi, T. Sumiya, M. Shoji, Angew. Chem. 2006, 118, 5653;
85. Angew. Chem. Int. Ed. 2006, 45, 5527;
86. d) D. Font, C. Jimeno, M. A. Pericàs, Org. Lett. 2006, 8, 4653;
87. e) Y. Wu, Y. Zhang, M. Yu, G. Zhao, S. Wang, Org. Lett. 2006, 8, 4417;
88. f) N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 734;
89. g) D. Font, S. Sayalero, A. Bastero, C. Jimeno, M. A. Pericàs, Org. Lett. 2008, 10, 337;
90. for Mannich reactions, see: h) L. Cheng, X. Wu, Y. Lu, Org. Biomol. Chem. 2007, 5, 1018;
91. i) Y. Hayashi, T. Urushima, S. Aratake, T. Okano, K. Obi, Org. Lett. 2008, 10, 21;
92. j) M. Amedjkouh, M. Brandberg, Chem. Commun. 2008, 3043.
93. For some selected examples of Michael reactions, see: k) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966;
94. l) S. Luo, X. Mi, S. Liu, H. Xu, J.-P. Cheng, Chem. Commun. 2006, 3687;
95. m) A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jørgensen, Chem. Commun. 2006, 4928;
96. n) V. Singh, V. K. Singh, Org. Lett. 2007, 9, 1117;
97. o) C. Palomo, A. Landa, A. Mielgo, M. Oiarbide, . Puente, S. Vera, Angew. Chem. 2007, 119, 8583;
98. Angew. Chem. Int. Ed. 2007, 46, 8431;
99. p) E. Alza, X. C. Cambeiro, C. Jimeno, M. A. Pericàs, Org. Lett. 2007, 9, 3717;
100. q) S. L. Zhu, S. Y. Yu, D. W. Ma, Angew. Chem. 2008, 120, 555;
101. Angew. Chem. Int. Ed. 2008, 47, 545;
102. r) S. Belot, A. Massaro, A. Tenti, A. Mordini, A. Alexakis, Org. Lett. 2008, 10, 4557;
103. s) J. Wang, F. Yu, X. Zhang, D. Ma, Org. Lett. 2008, 10, 2561;
104. t) Z. Mao, Y. Jia, W. Li, R. Wang, J. Org. Chem. 2010, 75, 7428.
105. a) Z. Zheng, B. L. Perkins, B. Ni, J. Am. Chem. Soc. 2010, 132, 50;
106. b) S. K. Ghosh, Z. Zheng, B. Ni, Adv. Synth. Catal. 2010, 352, 2378;
107. c) Q. Zhang, E. Parker, A. D. Headley, B. Ni, SynLett 2010, 2453;
108. d) D. Sarkar, R. Bhattarai, A. D. Headley, B. Ni, Synthesis 2011, 1993;
109. e) P. Chintala, S. K. Ghosh, E. Long, A. D. Headley, B. Ni, Adv. Synth. Catal. 2011, 353, 2905.
110. a) C. J. Li, T. H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997;
111. b) G.-J. ten Brink, I.W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636;
112. c) U. M. Lindstrçm, Chem. Rev. 2002, 102, 2751;
113. d) R. Breslow, Acc. Chem. Res. 1991, 24, 159;
114. e) S. Kobayashi, K. Manabe, Acc. Chem. Res. 2002, 35, 209;
115. f) S. Kobayashi, K. Manabe, Pure Appl. Chem. 2000, 72, 1373;
116. g) C. J. Li, Chem. Rev. 2005, 105, 3095;
117. h) N. Mase, C. F. Barbas III, Org. Biomol. Chem. 2010, 8, 4043;
118. i) M. Gruttadauria, F. Giacalone, R. Noto, Adv. Synth. Catal. 2009, 351, 33;
119. j) J. Paradowska, M. Stodulski, J. Mlynarski, Angew. Chem. 2009, 121, 4352;
120. Angew. Chem. Int. Ed. 2009, 48, 4288;
121. k) M. Raj, V. K. Singh, Chem. Commun. 2009, 6687.