A general aminocatalytic method for the synthesis of aldimines

Journal of the American Chemical Society

Volumn 136, Issue 3, 2014, Pages 1082-1089

  Morales, Sara ^a   Guijarro, Fernando G ^a   García Ruano, José Luis ^a   Cid, M Belén ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; ALDIMINES; BIOMIMETIC METHOD; CLASSICAL METHODS; IMINIUM; NUCLEOPHILIC CATALYSIS; ORGANOCATALYTIC; PYRROLIDINES;

NITROGEN COMPOUNDS;

BIOMIMETIC PROCESSES;

ALDEHYDE; ALKYL GROUP; CARBONYL DERIVATIVE; IMINE; KETONE; PHOSPHINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFONAMIDE;

ARTICLE; BIOMIMETICS; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; NUCLEOPHILICITY; ONE POT SYNTHESIS; OXIDATION; PH; SYNTHESIS;

AMINES; BIOMIMETICS; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; IMINES;

EID: 84892987286     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4111418     Document Type: Article

References (83)

1. Belowich, M. E.; Stoddart, J. F. Chem. Soc. Rev. 2012, 41, 2003 and references cited therein
2. Bloch, R. Chem. Rev. 1998, 98, 1407
3. Chiral Amine Synthesis: Methods, Developments and Applications; Nugent, T. C., Ed.; Wiley-VCH: Weinheim, Germany, 2010.
4. Tehrani, K. A.; De Kimpe, N. Sci. Synth. 2004, 27, 245
5. Charette, A. B. In Chiral Amine Synthesis: Methods, Developments and Applications; Nugent, T. C., Ed.; Wiley-VCH: Weinheim, Germany, 2010; Chapter 1.
6. MacMillan, D. W. C. Nature 2008, 455, 304
7. Gaunt, M. J.; Johansson, C. C. C.; McNally, A.; Vo, N. T. Drug Discovery Today 2007, 12, 8
8. Science of Synthesis: Asymmetric Organocatalysis; List, B.; Maruoka, K., Eds.; Thieme Chemistry: Stuttgart, Germany, 2012.
9. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471
10. Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416
11. Vicario, J. L.; Reyes, E.; Badia, D.; Carrillo, L. In Catalytic Asymmetric Conjugate Reactions; Cordova, A., Ed.; Wiley-VCH: Weinheim, Germany, 2010; Chapter 6.
12. Nielsen, M.; Worgull, D.; Zweifel, T.; Gschwend, B.; Bertelsen, S.; Jørgensen, K. A. Chem. Commun. 2011, 47, 632
13. Jurberg, I. D.; Chatterjee, I.; Tannert, R.; Melchiorre, P. Chem. Commun. 2013, 49, 4869
14. Knoevenagel, E. Chem. Ber. 1894, 27, 2345
15. Ingold, C. K. In Structure and Mechanism in Organic Chemistry; Cornell University Press: Ithaca, NY, 1953.
16. Crowell, T. I.; Peck, D. W. J. Am. Chem. Soc. 1953, 75, 1075
17. Schroeder, C.; Preis, S.; Link, K. P. Tetrahedron Lett. 1960, 1 (34) 23
18. Spencer, T. A. Studies of Amine Catalysis via Iminium Ion Formation. In Bioorganic Chemistry; Academic Press: New York, 1977; Chapter 13, pp 313-337.
19. McMurry, J. E.; Begley, T. P. The Organic Chemistry of Biological Pathways, 7 th ed.; Roberts and Company Publishers: Greenwood Village, CO, 2005.
20. Cordes, E. H.; Jencks, W. P. J. Am. Chem. Soc. 1962, 84, 826
21. Dirksen, A.; Hackeng, T. M.; Dawson, P. E. Angew. Chem., Int. Ed. 2006, 45, 7581
22. Dirksen, A.; Dirksen, S.; Hackeng, T. M.; Dawson, P. E. J. Am. Chem. Soc. 2006, 128, 15602
23. Kovaříček, P.; Lehn, J.-M. J. Am. Chem. Soc. 2012, 134, 9446
24. Wilhelms, N.; Kulchat, S.; Lehn, J.-M. Helv. Chim. Acta 2012, 95, 2635
25. Appel, R.; Chelli, S.; Tokuyasu, T.; Troshin, K.; Mayr, H. J. Am. Chem. Soc. 2013, 135, 6579
26. Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003
27. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984
28. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600
29. Davis, F. A.; Zhang, Y.; Andemichae, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403
30. Franzén, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296
31. Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212
32. 3)}. See: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60, 7037
33. García Ruano, J. L.; Alemán, J.; Fajardo, C.; Parra, A. Org. Lett. 2005, 7, 5493
34. García Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677
35. Jiang, Z.-Y.; Chan, W. H.; Lee, A. W. J. Org. Chem. 2005, 70, 1081
36. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, T. R.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555
37. García Ruano, J. L.; Alemán, J.; Cid, M. B.; Parra, A. Org. Lett. 2005, 7, 179
38. Higashibayashi, S.; Tohmiya, H.; Mori, T.; Hashimoto, K.; Nakata, M. Synlett 2004, 457
39. Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278
40. Forbes, D. C.; Bettigeri, S. V.; Amin, S. R.; Bean, C. J.; Law, A. M.; Stockman, R. A. Synth. Commun. 2009, 39, 2405
41. Marigo, M.; Schulte, T.; Franzén, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710
42. Dinér, P.; Nielsen, M.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983
43. Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396
44. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
45. Weinreb, S. M. Top. Curr. Chem. 1997, 190, 131
46. Gohain, N. Synlett 2003, 2097
47. Yoshida, K.; Akashi, N.; Yanagisawa, A. Tetrahedron: Asymmetry 2011, 22, 1225
48. Barbarotto, M.; Geist, J.; Choppin, S.; Colobert, F. Tetrahedron: Asymmetry 2009, 20, 2780
49. Regiani, T.; Santos, V. G.; Godoi, M. N.; Vaz, B. G.; Eberlin, M. N.; Coelho, F. Chem. Commun. 2011, 47, 6593
50. Fuyuhiko, T.; Ohyun, K.; Masaru, W.; Hannah, F. WO 2007111948, 2007.
51. Love, B. E.; Raje, P. S.; Williams, T. C., II. Synlett 1994, 493
52. Stokes, S.; Bekkam, M.; Rupp, M.; Mead, K. T. Synlett 2012, 389
53. Yamada, K.; Umeki, H.; Maekawa, M.; Yamamoto, Y.; Akindele, T.; Nakano, M.; Tomioka, K. Tetrahedron 2008, 64, 7258
54. AMS has been used to accelerate the formation of N-p -tolylsulfonyl imines and their use in tandem processes. See: Guo, Q.; Zhao, J. C.-G. Org. Lett. 2013, 15, 508
55. Primary amines and acidic additives have been used to sort out this problem and have been successfully employed for the Michael addition of unsaturated ketones via iminium activation. For example, see: Bartoli, G.; Melchiorre, P. Synlett 2008, 12, 1759
56. For a review, see: Weinreb, S. M.; Orr, R. K. Synthesis 2005, 1205
57. Desrosiers, J.-N.; Cote, A.; Boezio, A. A.; Charette, A. B. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5405
58. Desrosiers, J.-N.; Cote, A.; Boezio, A. A.; Charette, A. B. Org. Synth. 2006, 83, 5
59. Boyd, D. R.; Malone, J. F.; McGuckin, M. R.; Jennings, W. B.; Rutherford, M.; Saket, B. M. J. Chem. Soc., Perkin Trans. 2 1988, 1145
60. Krzyzanowska, B.; Stec, W. Synthesis 1978, 521
61. Krzyzanowska, B.; Stec, W. Synthesis 1982, 270
62. Banerjee, S.; Groeper, J. A.; Standard, J. M.; Hitchcock, S. R. Tetrahedron: Asymmetry 2009, 20, 2154
63. Jennings, W. B.; Lovely, C. J. Tetrahedron Lett. 1988, 29, 3725
64. 4 (5 equiv), refluxing DCM, 4 h. See: Bolshan, Y.; Batey, R. A. Org. Lett. 2005, 7, 1481
65. 4 (2 equiv), neat, MW, 70 C, 40 W, 10 min. See: Collados, J. F.; Toledano, E.; Guijarro, D.; Yus, M. J. Org. Chem. 2012, 77, 5744
66. 4, toluene, 45 C, 24 h. See: Huang, Z.; Zhang, M.; Wang, Y.; Qin, Y. Synlett 2005, 1334
67. 4 (5 equiv), DCM, rt, 5 h. See: Asada, M.; Obitsu, T.; Kinoshita, A.; Nagase, T.; Yoshida, T.; Yamaura, Y.; Takizawa, H.; Yoshikawa, K.; Sato, K.; Narita, M.; Nakai, H.; Toda, M.; Tobe, Y. Bioorg. Med. Chem. 2010, 18, 3212
68. Crisalli, P.; Kool, E. T. J. Org. Chem. 2013, 78, 1184
69. Crisalli, P.; Kool, E. T. Org. Lett. 2013, 15, 1646
70. Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75
71. Experimental procedure: cyanuric chloride (0.15 equiv), neat, 110 C, 2.5 h. See: Wua, L.; Yang, X.; Wang, X.; Yan, F. J. Sulfur Chem. 2010, 31, 509
72. This compound was prepared by MCPBA oxidation of the corresponding N -sulfinyl imine following the procedure of ref 26. The yield was not reported. See: Lanter, J. C.; Chen, H.; Zhang, X.; Sui, Z. Org. Lett. 2005, 7, 5905
73. For a method to form N -alkyl and N -aryl imines in water, see: Simion, A.; Simion, C.; Kanda, T.; Nagashima, S.; Mitoma, Y.; Yamada, T.; Mimura, K.; Tashiro, M. J. Chem. Soc., Perkin Trans. 1 2001, 2071
74. Patel, M. S.; Worsley, M. Can. J. Chem. 1970, 48, 1881
75. Samec, J. S. M.; Bäckvall, J.-E. Chem.-Eur. J. 2002, 8, 2955
76. Huang, L.; Zhang, Y.; Staples, R. J.; Huang, R. H.; Wulff, W. D. Chem.-Eur. J. 2012, 18, 5302
77. 2 (5 equiv), EtOH, US, rt, 10 min. See: Guzen, K. P.; Guarezemini, A. S.; Órfão, A. T. G.; Cella, R.; Pereira, C. M. P.; Stefani, H. A. Tetrahedron Lett. 2007, 48, 1845
78. Rodríguez-Solla, H.; Concellón, C.; Alvaredo, N.; Soengas, R. G. Tetrahedron 2012, 68, 1736
79. Künzi, S. A.; Morandi, B.; Carreira, E. M. Org. Lett. 2012, 14, 1900
80. A modified Wadsworth-Emmons procedure was used. See: Ciufolini, M. A.; Spencer, G. O. J. Org. Chem. 1989, 54, 4739
81. Vara, Y.; Bello, T.; Aldaba, E.; Arrieta, A.; Pizarro, J. L.; Arriortua, M. I.; López, X.; Cossio, F. P. Org. Lett. 2008, 10, 4759
82. 2 (5%), DCE, 8 h. See: Chakraborti, A. K.; Bhagat, S.; Rudrawar, S. Tetrahedron Lett. 2004, 45, 7641
83. Ciaccia, M.; Cacciapaglia, R.; Mencarelli, P.; Mandolini, L.; Di Stefano, S. Chem. Sci. 2013, 4, 2253