Polystyrene-supported TBD as an efficient and reusable organocatalyst for cyanosilylation of aldehydes, ketones, and imines

Tetrahedron Letters

Volumn 53, Issue 9, 2012, Pages 1075-1077

  Matsukawa, Satoru ^a   Fujikawa, Syohei ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

Basecatalyst; Cyanosilylation; Guanidine; Organocatalyst; Polymercatalyst

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; KETONE DERIVATIVE; POLYSTYRENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYANOSILYLATION;

EID: 84856213979     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.070     Document Type: Article

References (91)

1. Recent reviews, see C.A. McNamara, M.J. Dixon, and M. Bradley Chem. Rev. 102 2002 3275 3300
2. M. Benaglia, A. Puglisi, and F. Cozzi Chem. Rev. 103 2003 3401 3429
3. F. Cozzi Adv. Synth. Catal. 348 2006 1367 1390
4. W.J. Sommer, and M. Weck Cood. Chem. Rev. 251 2007 860 873
5. C.K. Kwong, R. Huang, M. Zhang, and P.H. Toy Chem. Eur. J. 13 2007 2369 2376
6. M.R. Buchmeiser Chem. Rev. 109 2009 303 321
7. Z. Wang, G. Chen, and K. Ding Chem. Rev. 109 2009 322 359
8. S. Ikegami, and H. Hamamoto Chem. Rev. 109 2009 583 593
9. J. Lu, and P.H. Toy Chem. Rev. 109 2009 815 838
10. T.E. Kristensen, and T. Hansen Eur. J. Org. Chem. 17 2010 3179 3204
11. M. Tomoi, Y. Kato, and H. Kakiuchi Macromol. Chem. 185 1984 2117 2124
12. K. Iijima, W. Fukuda, and M. Tomoi J. Macromol. Sci. Pure Appl. Chem. A29 1992 249 261
13. Y. Tamura, W. Fukuda, and M. Tomoi Synth. Commun. 24 1994 2907 2914
14. X. Xu, R. Mohan, and M.M. Morrissey Tetrahedron. Lett. 38 1997 7337 7340
15. S. Boisnard, J. Chastanet, and J. Zhu Tetrahedron Lett. 40 1999 7469 7472
16. D. Simoni, R. Rondanin, M. Morini, R. Baruchello, and F.P. Invidiata Tetrahedron Lett. 41 2000 1607 1610
17. PS-TBD as ligand in Cu-catalyzed 1,3-dipolar cycloaddition reaction, see: C. Coelho, P. Diz, O. Caamano, and E. Sotelo Adv. Synth. Catal. 352 2010 1179 1192
18. F. Fringuelli, F. Pizzo, C. Vittoriani, and L. Vaccaro Chem. Commun. 2004 2756 2757
19. F. Fringuelli, F. Pizzo, C. Vittoriani, and L. Vaccaro Eur. J. Org. Chem. 2006 1231 1236
20. D. Lanari, R. Balini, A. Palmieri, F. Pizzo, and L. Vaccaro Eur. J. Org. Chem. 2011 2874 2884
21. Silica-supported TBD catalyzed reactions have also been reported, see: Y.V.S. Rao, D.E. De Vos, and P.A. Jacobs Angew. Chem., Int. Ed. 36 1997 2661 2663
22. R. Ballini, G. Bosica, D. Fiorini, M. Raimondo, P. Righi, G. Sartori, and R. Sartorio Tetrahedron Lett. 43 2002 8445 8447
23. R. Ballini, D. Fiorini, R. Maggi, C. Oro, A. Palmieri, and G. Sartori Synlett 2006 1849 1850
24. R. Srivastava J. Mol. Cat. A: Chem. 264 2007 146 152
25. S. Matsukawa, N. Okano, and T. Imamoto Tetrahedron Lett. 41 2000 103 107
26. S. Matsukawa, and K. Obu Chem. Lett. 33 2004 1626 1627
27. S. Matsukawa, and E. Kitazaki Tetrahedron Lett. 49 2008 2982 2984
28. S. Matsukawa, and M. Saijo Tetrahedron Lett. 49 2008 4855 4857
29. S. Matsukawa, and K. Tsukamoto Org. Biomol. Chem. 7 2009 3792 3796
30. S. Matsukawa, I. Sekine, and A. Iitsuka Molecules 14 2009 3353 3359
31. D.A. Evans, and L.K. Truesdale Tetrahedron Lett. 1973 4929 4932
32. D.A. Evans, G.L. Carroll, and L.K. Truesdale J. Org. Chem. 39 1974 914 917
33. For recent reviews on synthesis and reactions of cyanohydrins, see: M. North Synlett 1993 807 820
34. J.H. Gregory Chem. Rev. 99 1999 3649 3682
35. M. North Tetrahedron: Asymmetry 14 2003 147 176
36. J.-M. Brunel, and I.P. Holmes Angew. Chem., Int. Ed. 43 2004 2752 2778
37. F.-X. Chen, and X. Feng Synlett 2005 892 899
38. N.H. Khan, R.I. Kureshy, S.H.R. Abdi, S. Agrawal, and R. Jasra Cood. Chem. Rev. 252 2008 593 623
39. For some recent asymmetric cyanations, see: Y. Hamashima, D. Sawada, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 121 1999 2641 2642
40. Y. Hamashima, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 122 2000 7412 7413
41. Y. Hamashima, D. Sawada, H. Nogami, M. Kanai, and M. Shibasaki Tetrahedron 57 2001 805 814
42. S.-K. Tian, and L. Deng J. Am. Chem. Soc. 123 2001 6195 6196
43. J. Tian, N. Yamagiwa, S. Matsunaga, and M. Shibasaki Angew. Chem., Int. Ed. 41 2002 3636 3638
44. J. Casas, C. Najera, J.M. Sansano, and J.M. Saa Org. Lett. 4 2002 2589 2592
45. Y.N. Belokon, A.J. Blacker, L.A. Clutterbuck, and M. North Org. Lett. 5 2003 4505 4507
46. S.-K. Tian, R. Hong, and L. Deng J. Am. Chem. Soc. 125 2003 9900 9901
47. J. Casas, A. Baeza, J.M. Sansano, C. Najera, and J.M. Saa Tetrahedron: Asymmetry 14 2003 197 200
48. N. Yamagiwa, J. Tian, S. Matsunaga, and M. Shibasaki J. Am. Chem. Soc. 127 2005 3413 3422
49. S. Lundgren, E. Wingstrand, M. Penhoat, and C. Moberg J. Am. Chem. Soc. 127 2005 11592 11593
50. M. Hatano, T. Ikeno, T. Miyamoto, and K. Ishihara J. Am. Chem. Soc. 127 2005 10776 10777
51. S. Gou, J. Wang, X. Liu, W. Wang, F.-X. Chen, and X. Feng Adv. Synth. Catal. 349 2007 343 349
52. R. Chinchilla, C. Najera, and F.J. Ortega Tetrahedron: Asymmetry 19 2008 265 268
53. M. Hatano, T. Ikeno, T. Matsumura, S. Torii, and K. Ishihara Adv. Synth. Catal. 350 2008 1776 1780
54. N.H. Khan, S. Agrawal, R.I. Kureshy, S.H.R. Abdi, K.J. Prathap, and R.V. Jasra Eur. J. Org. Chem. 2008 4511 4515
55. R. Chinchilla, C. Najera, F.J. Ortega, and S. Tari Tetrahedron: Asymmetry 20 2009 2279 2286
56. J. Wang, W. Wang, W. Li, X. Hu, K. Shen, C. Tan, X. Liu, and X. Feng Chem. Eur. J. 15 2009 11642 11659
57. N.H. Khan, S. Agrawal, R.I. Kureshy, S.H.R. Abdi, K. Pathak, and H.C. Bajaj Chirality 22 2010 153 158
58. M. North Angew. Chem., Int. Ed. 49 2010 8079 8081
59. C. Lv, C.G. Xia, and W. Sun Eur. J. Org. Chem. 2011 3407 3411
60. For recent reviews on Lewis base-catalyzed reactions, see: J. Gawronski, N. Wascinska, and J. Gajewy Chem. Rev. 108 2008 5227 5252
61. S.E. Denmark, and G.L. Beutner Angew. Chem., Int. Ed. 47 2008 1560 1638
62. S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama Chem. Lett. 1991 537 540
63. R. Córdoba, and J. Plumet Tetrahedron Lett. 44 2003 6157 6159
64. H. Zhou, F.-X. Chen, B. Qin, X. Feng, and G. Zhang Synlett 2004 1077 1079
65. Y. Li, B. He, X. Feng, and G. Zhang Synlett 2004 1598 1600
66. I. Amurrio, R. Córdoba, A.G. Csákÿ, and J. Plumet Tetrahedron 60 2004 10521 10524
67. A. Baeza, C. Najera, M.G. Retamosa, and J.M. Sansano Synthesis 2005 2787 2797
68. B. Fetterly, and J.G. Verkade Tetrahedron Lett. 46 2005 8061 8066
69. D.E. Fuerst, and E.N. Jacobsen J. Am. Chem. Soc. 127 2005 3547 3549
70. S.E. Denmark, and W. Chung J. Org. Chem. 71 2006 246 249
71. J.J. Song, F. Gallou, J.T. Reeves, Z. Tan, N.K. Yee, and C.H. Senanayake J. Org. Chem. 71 2006 1273 1276
72. L. Wang, X. Huang, J. Jun, X. Liu, and X. Feng Tetrahedron Lett. 47 2006 1581 1584
73. Y. Suzuki, A.B. Md, K. Muramatsu, and M. Sato Tetrahedron Lett. 47 2006 4227 4231
74. A.S. Paraskar, and A. Suladai Tetrahedron Lett. 47 2006 5759 5762
75. X. Wang, and S.-K. Tian Synlett 2007 1416 1420
76. X. Wang, and S.-K. Tian Tetrahedron Lett. 48 2007 6010 6013
77. I.V.P. Raj, G. Suryavanshi, and A. Suladai Tetrahedron Lett. 48 2007 7211 7214
78. M.G. Dekamin, J. Mokhtari, and M.R. Naimi-Jamal Cat. Commun. 10 2009 582 585
79. M.G. Dekamin, S. Sagheb-Asl, and M.R. Naimi-Jamal Tetrahedron Lett. 50 2009 4063 4066
80. S. Aoki, S. Kotani, M. Sugiura, and M. Nakajima Tetrahedron Lett. 51 2010 3547 3549
81. X. Wang, F. Fang, and S.-K. Tian Chin. Sci. Bull. 55 2010 2820 2823
82. Y.Q. Wen, W.M. Ren, and X.B. Lu Org. Biomol. Chem. 9 2011 6323 6330
83. Cyanosilylation using polymer-supported catalyst, see: G.M. Pawar, and M.R. Buchmeiser Adv. Synth. Catal. 352 2010 917 928
84. Y. Teng, and P.H. Toy Synlett 2011 551 554
85. Recent reviews on cyanosilylation with imines, see: S. Kobayashi, and H. Ishitani Chem. Rev. 99 1999 1069 1094
86. H. Groger Chem. Rev. 103 2003 2795 2827
87. P. Merino, E. Marqués-López, T. Tejero, and R.P. Herrera Tetrahedron 2009 1219 1234
88. S. Kobayashi, Y. Mori, J.S. Fossey, and M.M. Salter Chem. Rev. 111 2011 2626 2704
89. Organobase-catalyzed cyanosilylation with imines, see: R. Martínez, D.J. Ramón, and M. Yus Tetrahedron Lett. 46 2005 8471 8474
90. A.S. Paraskar, and A. Sudalai Tetrahedron Lett. 47 2006 5759 5762
91. I.V.P. Raj, G. Suryavanshi, and A. Sudalai Tetrahedron Lett. 48 2007 7211 7214