Asymmetric conjugate addition of ketones to β-nitrostyrenes by means of 1,2-amino-alcohol-derived prolinamides as bifunctional catalysts

European Journal of Organic Chemistry

Volumn , Issue 14, 2007, Pages 2328-2343

  Almaşi, Diana ^a   Alonso, Diego A ^a   Gómez Bengoa, Enrique ^b   Nagel, Yvonne ^a,c   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^c UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Amino acids; Asymmetric catalysis; Ketones; Michael addition

Indexed keywords

EID: 34250618376     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700031     Document Type: Article

References (94)

1. a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed 2001, 40, 3726-3748;
2. b) B. List, Tetrahedron 2002, 58, 5573-5590;
3. c) R. O. Duthaler, Angew. Chem. Int. Ed. 2003, 42, 975-978;
4. d) Acc. Chem. Res. 2004, 37 (8), special issue on organocatalysis;
5. e) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138-5175;
6. f) A. Berkessel, H. Gröger, in Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH, Weinheim, 2004;
7. g) P. M. Pihko, Angew. Chem. Int. Ed. 2004, 43, 2062-2064;
8. h) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719-724;
9. i) Tetrahedron 2006, 62 (2-3), Tetrahedron Symposium-in-Print on Organocatalysis in Organic Synthesis.
10. A. Perlmutter, Conjugative Additions in Organic Synthesis, Pergamon Press, Oxford, 1992.
11. For reviews on catalytic asymmetric Michael additions, see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061;
12. b) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196;
13. c) S. C. Jha, N. N. Joshi, Arkivoc 2002, vii, 167-196;
14. d) R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, M. Petrini, Chem. Rev. 2005, 105, 933-972;
15. e) D. Almasi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299-365.
16. a) N. Ono, The Nitro Group in Organic Synthesis Wiley-VCH: New York, 2001;
17. b) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894.
18. K. Sakthivel, W. Note, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267.
19. B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425.
20. D. Enders, A. Seki, Synlett 2002, 26-28.
21. a) O. Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal. 2004, 346, 1147-1168;
22. b) O. Andrey, A. Alexakis, G. Bernardinelli, Org. Lett. 2003, 5, 2559-2561.
23. T. Ishii, S. Fujioka, Y. Sekiguchi, H. Kotsuki, J. Am. Chem. Soc. 2004, 126, 9558-9559.
24. a) J. M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Synthesis 2004, 1509-1521;
25. b) N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 4966-4967.
26. A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84-96.
27. C. E. T. Mitchell, A. J. A. Cobb, S. V. Ley, Synlett 2005, 611-614.
28. D. Terakado, M. Takano, T. Oriyama, Chem. Lett. 2005, 34, 962-963.
29. S. B. Tsogoeva, D. A. Yalalov, M. J. Hateley, C. Weckbecker, K. Huthmacher, Eur. J. Org. Chem. 2005, 4995-5000.
30. Y. Xu, W. Zou, H. Sundén, I. Ibrahem, A. Córdova, Adv. Synth. Catal. 2006, 348, 418-424.
31. Y. Xu, A. Córdova, Chem. Commun. 2006, 460-462.
32. M.-K. Zhu, L. F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Tetrahedron: Asymmetry 2006, 17, 491-493.
33. D. A. Yalalov, S. B. Tsogoeva, S. Schmatz, Adv. Synth. Catal. 2006, 348, 826-, 832.
34. S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451-1453.
35. J. Wang, H. Li, B. Lou, L. Zu, H. Guo, W. Wang, Chem. Eur. J. 2006, 12, 4321-, 4332.
36. S. Luo, X. Mi, L. Zhang, S. Liu, H. Xu, J.-P. Cheng, Angew. Chem. Int. Ed. 2006, 45, 3093-3097.
37. C.-L. Cao, M.-C. Ye, X.-L. Sun, Y. Tang, Org. Lett. 2006, 8, 2901-2904.
38. H. Huang, E. N. Jacobsen, J. Am. Chem. Soc. 2006, 128, 7170-7171.
39. S. V. Pansare, K. J. Pandya, J. Am. Chem. Soc. 2006, 128, 9624-9625.
40. L. Zu, J. Wang, H. Li, W. Wang, Org. Lett. 2006, 8, 3077-3079.
41. S. Luo, X. Mi, S. Liu, H. Xu, J.-P. Cheng, Chem. Commun. 2006, 3687-3689.
42. a) Z. Tang, F. Jiang, L.-T. Yu, X. Cui, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Y.-D. Wu, J. Am. Chem. Soc. 2003, 125, 5262-5263;
43. b) Z. Tang, F. Jiang, X. Cui, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Y.-D. Wu, Proc. Natl. Acad. Sci. USA 2004, 101, 5755-5760;
44. c) Z. Tang, Z.-H. Yang, L.-F. Cun, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Org. Lett. 2004, 6, 2285-2287;
45. d) S. Tanimori, T. Naka, M. Kirihata, Synth. Commun. 2004, 34, 4043-4048;
46. e) Z. Tang, Z.-H. Yang, X.-H. Cheng, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, J. Am. Chem. Soc. 2005, 127, 9285-9289;
47. f) J.-R. Chen, H.-H. Lu, X.-Y. Li, L. Cheng, J. Wan, W.-J. Xiao, Org. Lett. 2005, 7, 4543-4545;
48. g) D. Gryko, R. Lipiński, Adv. Synth. Catal. 2005, 347, 1948-1952;
49. h) S. Samanta, J. Liu, R. Dodda, C.-G. Zhao, Org. Lett. 2005, 7, 5321-5323;
50. i) L. He, Z. Tang, L. F. Cun, A.-Q. Mi, Y.-Z. Jiang, L. Z. Gong, Tetrahedron 2006, 62, 346-351;
51. j) M. Jiang, S.-F. Zhu, Y. Yang, L.-Z. Gong, X.-G. Zhou, Q.-L. Zhou, Tetrahedron: Asymmetry 2006, 17, 384-387;
52. k) Z. Tang, L.-F. Cun, X. Cui, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, Org. Lett. 2006, 8, 1263-1266;
53. l) G. Guillena, M. C. Hita, C. Nájera, Tetrahedron: Asymmetry 2006, 17, 729-733;
54. m) G. Guillena, M. C. Hita, C. Nájera, Tetrahedron: Asymmetry 2006, 17, 1027-1031;
55. n) G. Guillena, M. C. Hita, C. Najera, Tetrahedron: Asymmetry 2006,17, 1493-1497;
56. o) D. Gryko, B. Kowalczyk, L. Zawadzki, Synlett 2006, 1059-1062;
57. p) S. Samanta, C.-G. Zhao, J. Am. Chem. Soc. 2006, 128, 7442-7443;
58. q) M. Raj, V. S. K. Ginotra, V. K. Singh, Org Lett. 2006, 8, 4097-4099;
59. r) J.-R. Chen, X.-Y. Li, X.-N. Xing, W.-J. Xiao, J. Org. Chem. 2006, 71, 8198-8202.
60. H.-M. Guo, L.-F. Cun, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Chem. Commun. 2005, 1450-1452.
61. S. S. Chimni, D. Mahajan, V. V. S. Babu, Tetrahedron Lett. 2005, 46, 5617-5619.
62. H.-M. Guo, L. Cheng, L.-F. Cun, L.-Z. Gong, A.-Q. Mi, Y.-Z. Jiang, Chem. Commun. 2006, 429-431.
63. a) W. Wang, J. Wang, H. Li, Org. Lett. 2004, 6, 2817-2820;
64. b) J. Wang, H. Li, Y. Mei, B. Lou, D. Xu, D. Xie, H. Guo, W. Wang, J. Org. Chem. 2005, 70, 5678-5687.
65. N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 4790-4791.
66. a) J. Hine, Acc. Chem. Res. 1978, 11, 1-7;
67. b) J. Hine, Y. Chou, J. Org. Chem. 1981, 46, 649-652;
68. c) S. Saito, H. Yamamoto, Ace. Chem. Res. 2004, 37, 570-579.
69. D. Almasi, D. A. Alonso, C. Najera, Tetrahedron: Asymmetry 2006, 17, 2064-2068.
70. Z. J. Song, M. Zhao, R. Desmond, P. Devine, D. M. Tschaen, R. Tillyer, L. Frey, R. Heid, F. Xu, B. Foster, J. Li, R. Reamer, R. Volante, E. J. J. Grabowski, U. H. Dolling, P. J. Reider, S. Okada, Y. Kato, E. Mano, J. Org. Chem. 1999, 64, 9658-9667.
71. R. E. Gawley, P. Zhang, J. Org. Chem. 1996, 61, 8103-8112.
72. [7]
73. N. Vignola, B. List, J. Am. Chem. Soc. 2004, 126, 450-451.
74. For the asymmetric α-aminoxylation, O-nitroso-aldol/Michael and Mannich reactions with carbonyl compounds, see: a) Y. Hayashi, J. Yamaguchi, K. Hibino, T. Sumiya, T. Urushima, M. Shoji, D. Hashizume, H. Koshino, Adv. Synth. Catal. 2004, 346, 1435-1439;
75. For the asymmetric Michael reaction of aldehydes and nitro alkanes, see: b) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. Int. Ed. 2005, 44, 4212-4215;
76. For the asymmetric Mannich reaction, see: c) D. Enders, C. Grondal, M. Vrettou, G. Raabe, Angew. Chem. Int. Ed. 2005, 44, 4079-4083;
77. For the α-fluorination of aldehydes and ketones, see: d) D. Enders, M. R. M. Hüttl, Synlett 2005, 991-993;
78. For the asymmetric aldol reaction in the synthesis of carbohydrates, see: e) C. Grondal, D. Enders, Tetrahedron 2006, 62, 329-337.
79. At this point, catalysts 21f and 21g were also tested in order to confirm 21e as the best choice. Compound 21f gave a 65% yield, a synlanti of 84:14 and a 74% ee after a 6d reaction, whereas 21g gave a 45% yield, a synlanti of 80:20 and a 78% ee after a 7 d reaction.
80. a) M. E. Kuehne, J. Am. Chem. Soc. 1959, 81, 5400-5404;
81. b) T. A. Spencer, H. S. Neel, D. C. Ward, K. L. Williamson, J. Org. Chem. 1966, 31, 434-436;
82. c) R. B. Woodward, Pure Appl. Chem. 1968, 17, 519-547;
83. d) Z. G. Hajos, D. R. Parrosh, J. Org. Chem. 1974, 39, 1612-1615.
84. Y. Zhou, Z. Shah, Tetrahedron: Asymmetry 2006, 17, 1671-1677.
85. See the supporting information.
86. C. Girard, H. B. Kagan, Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
87. D. Seebach, J. Golinski, Helv. Chim. Acta 1981, 64, 1413-1423.
88. Calculations were carried out using the GAUSSIAN 03 suite of programs: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, GAUSSIAN 03, Revision C.02, Gaussian, Inc., Wallingford CT, 2004.
89. R. G. Parr, W. Yang, in Density-Functional Theory of Atoms and Molecules, Oxford, New York, 1989.
90. a) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
91. b) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
92. c) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
93. d) W. Kohn, A. D. Becke, R. G. Parr, J. Phys. Chem. 1996, 100, 12974-12980.
94. [21]