Polymer-supported enantioselective bifunctional catalysts for nitro-Michael addition of ketones and aldehydes

Chemistry - A European Journal

Volumn 18, Issue 8, 2012, Pages 2290-2296

  Tuchman Shukron, Lital ^a   Miller, Scott J ^b   Portnoy, Moshe ^a  

^a TEL AVIV UNIVERSITY   (Israel)

^b YALE UNIVERSITY   (United States)

Author keywords

asymmetric catalysis; bifunctional catalysis; immobilization; nitro Michael addition; organocatalysis

Indexed keywords

AMINE CATALYSTS; ASYMMETRIC ADDITION; ASYMMETRIC CATALYSIS; BI-FUNCTIONAL CATALYSTS; BIFUNCTIONAL; BIFUNCTIONAL CATALYSIS; BOND FORMING; CATALYTIC REACTIONS; CYCLOPENTANONE; D-AMINO ACID; ELECTRON WITHDRAWING GROUP; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; IMMOBILIZED CATALYSTS; L-AMINO ACIDS; NITRO-MICHAEL ADDITION; NITROOLEFINS; ORGANOCATALYSIS; POLYMER-SUPPORTED; SIDE-CHAINS; TRANSITION STATE;

ACETONE; ADDITION REACTIONS; ALDEHYDES; AMINO ACIDS; CATALYSIS; CATALYST ACTIVITY; ENANTIOSELECTIVITY; ISOMERS; METABOLISM; RADIOACTIVE WASTE VITRIFICATION; REACTION KINETICS; UREA;

CATALYST SUPPORTS;

EID: 84863412247     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102474     Document Type: Article

References (128)

1. R. Rios, A. Moyano, in Catalytic Asymmetric Conjugate Reactions, (Ed.:, A. Cordova,), Wiley-VCH, Weinheim, 2010, pp. 191-218
2. H. Pellissier, Recent Development in Asymmetric Organocatalysis, RSC Publishing, Cambridge, 2010, pp. 1-76.
3. S. Sulzer-Mossé, A. Alexakis, Chem. Commun. 2007, 3123-3135
4. S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716
5. J. Vicario, D. Badía, L. Carrillo, Synthesis 2007, 2065-2092
6. D. Almaşi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299-365.
7. N. Ono, The Nitro Group in Organic Synthesis Wiley-VCH, New York, 2001, p
8. O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894
9. R. Ballini, M. Petrini, Tetrahedron 2004, 60, 1017-1047.
10. E. Alza, M. A. Pericas, Adv. Synth. Catal. 2009, 351, 3051-3056
11. T. Miao, L. Wang, Tetrahedron Lett. 2008, 49, 2173-2176
12. E. Alza, X. C. Cambeiro, C. Jimeno, M. A. Pericas, Org. Lett. 2007, 9, 3717-3720
13. P. Li, L. Wang, M. Wang, Y. Zhang, Eur. J. Org. Chem. 2008, 2008, 1157-1160
14. P. Li, L. Wang, Y. Zhang, G. Wang, Tetrahedron 2008, 64, 7633-7638
15. Y.-B. Zhao, L.-W. Zhang, L.-Y. Wu, X. Zhong, R. Li, J.-T. Ma, Tetrahedron: Asymmetry 2008, 19, 1352-1355
16. S. Luo, J. Li, L. Zhang, H. Xu, J. P. Cheng, Chem. Eur. J. 2008, 14, 1273-1281
17. J. Liu, P. Li, Y. Zhang, K. Ren, L. Wang, G. Wang, Chirality 2010, 22, 432-441
18. Y. Chuan, G. Chen, Y. Peng, Tetrahedron Lett. 2009, 50, 3054-3058
19. M. C. Varela, S. M. Dixon, K. S. Lam, N. E. Schore, Tetrahedron 2008, 64, 10087-10090.
20. refs. [4b-i]
21. C. L. Cao, M. C. Ye, X. L. Sun, Y. Tang, Org. Lett. 2006, 8, 2901-2904
22. S. V. Pansare, K. Pandya, J. Am. Chem. Soc. 2006, 128, 9624-9625
23. H. Chen, Y. Wang, S. Wei, J. Sun, Tetrahedron: Asymmetry 2007, 18, 1308-1312
24. F. Y. Liu, S. W. Wang, N. Wang, Y. G. Peng, Synlett 2007, 2415-2419
25. G. L. Puleo, A. Iuliano, Tetrahedron: Asymmetry 2008, 19, 2045-2050
26. A. P. Carley, S. Dixon, J. D. Kilburn, Synthesis 2009, 2509-2516
27. A. D. Lu, P. Gao, Y. Wu, Y. M. Wang, Z. H. Zhou, C. C. Tang, Org. Biomol. Chem. 2009, 7, 3141-3147
28. S. V. Pansare, R. L. Kirby, Tetrahedron 2009, 65, 4557-4561.
29. L. Gu, Y. Wu, Y. Zhang, G. Zhao, J. Mol. Catal. A: Chem 2007, 263, 186-194
30. B. K. Ni, Q. Y. Zhang, K. Dhungana, A. D. Headley, Org. Lett. 2009, 11, 1037-1040
31. G. Lv, R. Jin, W. Mai, L. Gao, Tetrahedron: Asymmetry 2008, 19, 2568-2572
32. N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas, J. Am. Chem. Soc. 2006, 128, 4966-4967
33. C. F. Barbas III, J. M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, Synthesis 2004, 2004, 1509-1521
34. J. Wang, H. Li, B. Lou, L. Zu, H. Guo, W. Wang, Chem. Eur. J. 2006, 12, 4321-4332
35. Vishnumaya, V. K. Singh, Org. Lett. 2007, 9, 1117-1119
36. L.-Y. Wu, Z.-Y. Yan, Y.-X. Xie, Y.-N. Niu, Y.-M. Liang, Tetrahedron: Asymmetry 2007, 18, 2086-2090
37. B. Ni, Q. Zhang, A. D. Headley, Tetrahedron Lett. 2008, 49, 1249-1252
38. D. Diez, M. Jose Gil, R. F. Moro, I. S. Marcos, P. García, P. Basabe, N. M. Garrido, H. B. Broughton, J. G. Urones, Tetrahedron 2007, 63, 740-747
39. S. Mossé, M. Laars, K. Kriis, T. Kanger, A. Alexakis, Org. Lett. 2006, 8, 2559-2562
40. M. T. Barros, A. M. Faísca Phillips, Eur. J. Org. Chem. 2007, 2007, 178-185.
41. L. Tuchman-Shukron, M. Portnoy, Adv. Synth. Catal. 2009, 351, 541-546.
42. D. A. Yalalov, S. B. Tsogoeva, S. Schmatz, Adv. Synth. Catal. 2006, 348, 826-832
43. S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451-1453
44. H. B. Huang, E. N. Jacobsen, J. Am. Chem. Soc. 2006, 128, 7170-7171
45. T. Mandal, C.-G. Zhao, Angew. Chem. 2008, 120, 7828-7831
46. Angew. Chem. Int. Ed. 2008, 47, 7714-7717
47. Z. Yang, J. Liu, X. Liu, Z. Wang, X. Feng, Z. Su, C. Hu, Adv. Synth. Catal. 2008, 350, 2001-2006.
48. Y. Xu, W. Zou, H. Sundén, I. Ibrahem, A. Cõrdova, Adv. Synth. Catal. 2006, 348, 418-424
49. S. Luo, X. Mi, L. Zhang, S. Liu, H. Xu, J. P. Cheng, Angew. Chem. 2006, 118, 3165-3169
50. Angew. Chem. Int. Ed. 2006, 45, 3093-3097
51. S. Z. Luo, H. Xu, X. L. Mi, J. Y. Li, X. X. Zheng, J.-P. Cheng, J. Org. Chem. 2006, 71, 9244-9247.
52. E. A. C. Davie, S. M. Mennen, Y. J. Xu, S. J. Miller, Chem. Rev. 2007, 107, 5759-5812
53. M. Wiesner, M. Neuburger, H. Wennemers, Chem. Eur. J. 2009, 15, 10103-10109.
54. M. P. Lalonde, Y. Chen, E. N. Jacobsen, Angew. Chem. 2006, 118, 6514-6518
55. Angew. Chem. Int. Ed. 2006, 45, 6366-6370.
56. ref. [10b]
57. ref. [11]
58. M. Wiesner, J. D. Revell, H. Wennemers, Angew. Chem. 2008, 120, 1897-1900
59. Angew. Chem. Int. Ed. 2008, 47, 1871-1874
60. L. Zu, H. Li, J. Wang, X. Yu, W. Wang, Tetrahedron Lett. 2006, 47, 5131-5134
61. J.-R. Chen, Y.-Q. Zou, L. Fu, F. Ren, F. Tan, W.-J. Xiao, Tetrahedron 2010, 66, 5367-5372.
62. T. Okino, Y. Hoashi, T. Furukawa, X. N. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119-125
63. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673.
64. R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860
65. J. Quick, C. Mondello, M. Humora, T. Brennan, J. Org. Chem. 1978, 43, 2705-2708.
66. A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005, pp. 45-84
67. C. Bressy, P. I. Dalko, in Enantioselective Organocatalysis, (Ed. , P. I. Dalko,), Wiley-VCH, Weinheim, 2007, pp. 77-94.
68. refs. [5c-e]
69. refs. [6d-i]
70. ref. [9b]
71. T. Ishii, S. Fujioka, Y. Sekiguchi, H. Kotsuki, J. Am. Chem. Soc. 2004, 126, 9558-9559
72. S. Luo, X. Mi, S. Liu, H. Xu, J. P. Cheng, Chem. Commun. 2006, 3687-3689
73. T. Mandal, C. G. Zhao, Tetrahedron Lett. 2007, 48, 5803-5806
74. C. Wang, C. Yu, C. Liu, Y. Peng, Tetrahedron Lett. 2009, 50, 2363-2366
75. D.-Q. Xu, L.-P. Wang, S.-P. Luo, Y.-F. Wang, S. Zhang, Z.-Y. Xu, Eur. J. Org. Chem. 2008, 2008, 1049-1053
76. D. Q. Xu, H. D. Yue, S. P. Luo, A. B. Xia, S. Zhang, Z. Y. Xu, Org. Biomol. Chem. 2008, 6, 2054-2057.
77. refs. [12c], [12d]
78. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287
79. Angew. Chem. Int. Ed. 2005, 44, 4212-4215
80. C. Palomo, S. Vera, A. Mielgo, E. Gomez-Bengoa, Angew. Chem. 2006, 118, 6130-6133
81. Angew. Chem. Int. Ed. 2006, 45, 5984-5987
82. J. B. Wu, B. K. Ni, A. D. Headley, Org. Lett. 2009, 11, 3354-3356.
83. refs. [4d-g]
84. refs. [5b-c]
85. refs. [6b-h]
86. refs. [9b-c]
87. ref. [17g]
88. A. Alexakis, O. Andrey, Org. Lett. 2002, 4, 3611-3614.
89. ref. [4h]
90. ref. [8d]
91. ref. [17f]
92. ref. [17h]
93. A. Lu, R. Wu, Y. Wang, Z. Zhou, G. Wu, J. Fang, C. Tang, Eur. J. Org. Chem. 2010, 2010, 2057-2061
94. A. Lu, R. Wu, Y. Wang, Z. Zhou, G. Wu, J. Fang, C. Tang, Eur. J. Org. Chem. 2011, 2011, 122-127.
95. refs. [4c-h]
96. refs. [5b], [5d]
97. refs. [6a-e]
98. refs. [6g-j]
99. ref. [9b]
100. refs. [17g], [17i]
101. ref. [20f]
102. B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425
103. D. Enders, A. Seki, Synlett 2002, 26-28
104. O. Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal. 2004, 346, 1147-1168
105. A. J. Cobb, D. A. Longbottom, D. M. Shaw, S. V. Ley, Chem. Commun. 2004, 1808-1809.
106. ref. [4i]
107. ref. [8d].
108. refs. [4a], [4d]
109. ref. [5b]
110. refs. [6d], [6k], [6l]
111. ref. [9b]
112. ref. [18b], d
113. ref. [20f]
114. Q. Tao, G. Tang, K. Lin, Y. F. Zhao, Chirality 2008, 20, 833-838
115. N. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 2527-2530
116. L. S. Zu, J. Wang, H. Li, W. Wang, Org. Lett. 2006, 8, 3077-3079.
117. X. J. Zhang, S. P. Liu, X. M. Li, M. Yan, A. S. Chan, Chem. Commun. 2009, 833-835.
118. C. G. Kokotos, G. Kokotos, Adv. Synth. Catal. 2009, 351, 1355-1362
119. B.-L. Li, Y.-F. Wang, S.-P. Luo, A.-G. Zhong, Z.-B. Li, X.-H. Du, D.-Q. Xu, Eur. J. Org. Chem. 2010, 2010, 656-662
120. Q. Gu, X.-T. Guo, X.-Y. Wu, Tetrahedron 2009, 65, 5265-5270.
121. J. Bures, A. Armstrong, D. G. Blackmond, J. Am. Chem. Soc. 2011, 133, 8822-8825
122. K. Patora-Komisarska, M. Benohoud, H. Ishikawa, D. Seebach, Y. Hayashi, Helv. Chim. Acta 2011, 94, 719-745.
123. Y. Arakawa, M. Wiesner, H. Wennemers, Adv. Synth. Catal. 2011, 353, 1201-1206.
124. X.-Y. Cao, J.-C. Zheng, Y.-X. Li, Z.-C. Shu, X.-L. Sun, B.-Q. Wang, Y. Tang, Tetrahedron 2010, 66, 9703-9707
125. D. A. Evans, S. Mito, D. Seidel, J. Am. Chem. Soc. 2007, 129, 11583-11592
126. E. Juaristi, A. K. Beck, J. Hansen, T. Matt, T. Mukhopadhyay, M. Simson, D. Seebach, Synthesis 1993, 1271-1290
127. J. Wang, H. Li, W. Duan, L. Zu, W. Wang, Org. Lett. 2005, 7, 4713-4716
128. F. Xue, S. Zhang, W. Duan, W. Wang, Adv. Synth. Catal. 2008, 350, 2194-2198.