Copper complex of aminoisoborneol schiff base Cu 2(SBAIB-d) 2: An efficient catalyst for direct catalytic asymmetric nitroaldol (henry) reaction

Advanced Synthesis and Catalysis

Volumn 354, Issue 13, 2012, Pages 2511-2520

  Boobalan, Ramalingam ^a   Lee, Gene Hsian ^b   Chen, Chinpiao ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

asymmetric catalysis; copper(II) complexes; enantioselectivity; Henry reaction; Schiff bases

Indexed keywords

EID: 84865731304     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200337     Document Type: Article

References (84)

1. F. A. Luzzio, Tetrahedron 2001, 57, 915-945
2. J. Boruwa, N. Gogoi, P. P. Saikia, N. C. Barua, Tetrahedron: Asymmetry 2006, 17, 3315-3326
3. C. Palomo, M. Oiarbide, A. Laso, Eur. J. Org. Chem. 2007, 2561-2574
4. G. Blay, V. Henandez-Olmos, J. R. Pedro, Synlett 2011, 1195-1211.
5. H. Sasai, T. Suzuki, S. Arai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1992, 114, 4418-4420.
6. C. Christensen, K. Juhl, K. A. Jorgensen, J. Org. Chem. 2002, 67, 4875-4881
7. D. A. Evans, D. Seidel, M. Rueping, H. W. Lam, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2003, 125, 12692-12693
8. H. Maheswaran, K. L. Prasanth, G. G. Krishna, K. Ravikumar, B. Sridhar, M. L. Kantam, Chem. Commun. 2006, 4066-4068
9. K. Y. Ma, J. S. You, Chem. Eur. J. 2007, 13, 1863-1871
10. B. Qin, X. Xiao, X. H. Liu, J. L. Huang, Y. H. Wen, X. M. Feng, J. Org. Chem. 2007, 72, 9323-9328
11. M. Bandini, M. Benaglia, R. Sinisi, S. Tommasi, A. Umani-Ronchi, Org. Lett. 2007, 9, 2151-2153
12. Y. Xiong, F. Wang, X. Huang, Y. H. Wen, X. Feng, Chem. Eur. J. 2007, 13, 829-833
13. T. Arai, M. Watanabe, A. Yanagisaka, Org. Lett. 2007, 9, 3595-3597
14. G. Blay, E. Climent, I. Fernandez, V. Hernandez, J. R. Pedro, Tetrahedron: Asymmetry 2007, 18, 1603-1612
15. M. Bandini, F. Picinelli, S. Tommasi, A. Umani-Ronchi, C. Ventrici, Chem. Commun. 2007, 616-618
16. G. Blay, L. R. Domingo, V. Hernandez-Olmos, J. R. Pedro, Chem. Eur. J. 2008, 14, 4725-4730
17. K. Y. Spangler, C. Wolf, Org. Lett. 2009, 11, 4724-4727
18. G. Q. Zhang, E. Yashima, W. D. Woggon, Adv. Synth. Catal. 2009, 351, 1255-1262
19. M. Breuning, D. Hein, M. Steiner, V. H. Gessner, C. Strohmann, Chem. Eur. J. 2009, 15, 12764-12769
20. A. Noole, K. Lippur, A. Metsala, M. Lopp, T. Kanger, J. Org. Chem. 2010, 75, 1313-1316
21. M. Steurer, C. Bolm, J. Org. Chem. 2010, 75, 3301-3310
22. L. Cheng, J. Dong, J. You, G. Gao, J. Lan, Chem. Eur. J. 2010, 16, 6761-6765
23. W. Jin, X. Li, Y. Huang, F. Wu, B. Wan, Chem. Eur. J. 2010, 16, 8259-8261
24. I. Panov, P. Drabina, Z. Padelkova. P. Simunek, M. Sedlak, J. Org. Chem. 2011, 76, 4787-4793
25. D. Didier, C. Magnier-Bouvier, E. Schulza, Adv. Synth. Catal. 2011, 353, 1087-1095
26. G. Lai, F. Guo, Y. Zheng, Y. Fang, H. Song, K. Xu, S. Wang, Z. Zha, Z. Wang, Chem. Eur. J. 2011, 17, 1114-1117
27. Y. Q. Ji, G. Qi, Z. M. A. Judeh, Eur. J. Org. Chem. 2011, 4892-4898.
28. B. M. Trost, V. S. C. Yeh, Angew. Chem. 2002, 114, 889-891
29. Angew. Chem. Int. Ed. 2002, 41, 861-863
30. C. Palomo, M. Oiarbide, A. Laso, Angew. Chem. 2005, 117, 3949-3952
31. Angew. Chem. Int. Ed. 2005, 44, 3881-3884
32. S. Liu, C. Wolf, Org. Lett. 2008, 10, 1831-1834
33. A. Bulut, A. Aslan, O. Dogan, J. Org. Chem. 2008, 73, 7373-7375.
34. R. Kowalczyk, L. Sidorowicz, J. Skarzewaski, Tetrahedron: Asymmetry 2007, 18, 2581-2586
35. R. Kowalczyk, P. Kwiatkowski, J. Skarzewski, J. Jurczak, J. Org. Chem. 2009, 74, 753-756
36. A. Zulauf, M. Mellah, E. Schulz, J. Org. Chem. 2009, 74, 2242-2245.
37. Y. Kogami, T. Nakajima, T. Ikeno, T. Yamada, Synthesis 2004, 1947-1950
38. J. Park, K. Lang, K. A. Abboud, S. Hong, J. Am. Chem. Soc. 2008, 130, 16484-16485.
39. H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 60, 7388-7389
40. S. Handa, K. Nagawa, Y. Sohtome, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 3274-3277
41. Angew. Chem. Int. Ed. 2008, 47, 3230-3233
42. T. Nitabaru, A. Nojiri, M. Kobayashi, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 13860-13869.
43. Reference for rare earth metal-catalyzed asymmetric Henry reaction:, B. M. Choudary, K. V. S. Ranganath, U. Pal, M. L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 2005, 127, 13167-13171.
44. E. J. Corey, F. Y. Zhang, Angew. Chem. 1999, 111, 2057-2059
45. Angew. Chem. Int. Ed. 1999, 38, 1931-1934
46. T. Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 2054-2055
47. Y. Sohtome, Y. Hashimoto, K. Nagasawa, Adv. Synth. Catal. 2005, 347, 1643-1648
48. H. M. Li, B. M. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 732-733
49. T. Marcelli, R. N. S. van der Haas, J. H. van Maarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 943-945
50. Angew. Chem. Int. Ed. 2006, 45, 929-931
51. Y. Sohtome, Y. Hashimoto, K. Nagasawa, Eur. J. Org. Chem. 2006, 2894-2897
52. T. Mandal, S. Samanta, C. G. Zhao, Org. Lett. 2007, 9, 943-945
53. M. Bandini, R. Sinisi, A. Umani-Ronchi, Chem. Commun. 2008, 4360-4362
54. K. Kanagaraj, P. Suresh, K. Pitchumani, Org. Lett. 2010, 12, 4070-4073.
55. T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skrane, D. Mink, H. Griengl, Angew. Chem. 2006, 118, 3532-3535
56. Angew. Chem. Int. Ed. 2006, 45, 3454-3456
57. M. G. Khadjawi, T. Purkarthofer, W. Skrane, H. Griengl, Adv. Synth. Catal. 2007, 349, 1445-1450.
58. Z. B. Li, L. Pu, Org. Lett. 2004, 6, 1065-1068
59. C. Chen, L. Hong, Z. Q. Xu, L. Liu, R. Wang, Org. Lett. 2006, 8, 2277-2280
60. Z. B. Li, T. D. Liu, L. Pu, J. Org. Chem. 2007, 72, 4340-4343
61. E. M. McGarrigle, D. G. Gilheany, Chem. Rev. 2005, 105, 1563-1602
62. P. J. Walsh, H. Li, C. A. de Parrodi, Chem. Rev. 2007, 107, 2503-2545
63. T. Niimi, T. Uchida, R. Irie, T. Katsuki, Adv. Synth. Catal. 2001, 343, 79-88
64. H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781
65. Y. Kato, M. Furutachi, Z. Chen, H. Mitsunuma, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 9168-9169
66. Q. Fan, L. Lin, J. Liu, Y. Huang, X. Feng, G. Zhang, Org. Lett. 2004, 6, 2185-2188
67. Y. Yasutomi, H. Suematsu, T. Katsuki, J. Am. Chem. Soc. 2010, 132, 4510-4511.
68. C. Gan, G. Lai, Z. Zhang, Z. Wang, M.-M. Zhoub, Tetrahedron: Asymmetry 2006, 17, 725-728
69. J.-J. Jianga, M. Shi, Tetrahedron: Asymmetry 2007, 18, 1376-1382
70. G. Lai, S. Wang, Z. Wang, Tetrahedron: Asymmetry 2008, 19, 1813-1819
71. J. Guo, J. Mao, Chirality 2009, 21, 619-627
72. M. L. Ingalsbe, J. D. St. Denis, J. L. Gleason, G. P. Savage, R. Priefer, Synthesis 2010, 98-102
73. D. Xin, Y. Ma, F. He, Tetrahedron: Asymmetry 2010, 21, 333-338
74. G. Oztürk, M. Colak, N. Demirel, Chirality 2011, 23, 374-378.
75. X.-R. Huang, C. Chen, G.-H. Lee, S.-M. Peng, Adv. Synth. Catal. 2009, 351, 3089-3095
76. X.-R. Huang, X.-H. Pan, G.-H. Lee, C. Chen, Adv. Synth. Catal. 2011, 353, 1949-1954
77. R. Boobalan, C. Chen, G. H. Lee, Org. Biomol. Chem. 2012, 10, 1625-1638.
78. S. Handa, K. Nagawa, Y. Sohtome, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 3274-3277
79. Angew. Chem. Int. Ed. 2008, 47, 3230-3233
80. T. Arai, R. Takashita, Y. Endo, M. Watanabe, A. Yanagisawa, J. Org. Chem. 2008, 73, 4903-4906
81. H. Y. Kim, K. Oh, Org. Lett. 2009, 11, 5682-5685
82. S. Selvakumar, D. Sivasankaran, V. K. Singh, Org. Biomol. Chem. 2009, 7, 3156-3162
83. W. Jin, X. Li, B. Wan, J. Org. Chem. 2011, 76, 484-491
84. Y. Zhou, J. Dong, F. Zhang, Y. Gong, J. Org. Chem. 2011, 76, 588-600.