Catalytic enantioselective Aza-Henry reactions

European Journal of Organic Chemistry

Volumn , Issue 15, 2009, Pages 2401-2420

  Marques Lopez E ^a   Merino, P ^b   Tejero, T ^b   Herrera, R P ^b,c  

^a TU DORTMUND UNIVERSITY   (Germany)

^b CSIC   (Spain)

^c FUNDACIÓN ARAID   (Spain)

Author keywords

Asymmetric catalysis; Aza henry reactions; Enantioselectivity; Nitro mannich reactions; Nucleophilic addition

Indexed keywords

EID: 66149117034     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801097     Document Type: Article

References (110)

1. a) C. Anaya de Parrodi, E. Juaristi, Synlett 2006, 2699-2715;
2. b) G. Martelli, D. Savoia, Curr. Org. Chem. 2003, 7, 1049-1070;
3. c) M. S. Mortensen, G. A. O'Doherty, Chemtracts 2005, 18, 555-561.
4. For a highlight, see: B. Westermann, Angew. Chem. Int. Ed. 2003, 42, 151-153.
5. R. Ballini, M. Petrini, Tetrahedron 2004, 60, 1017-1047. For the application of this approach to the synthesis of optically active a-amino acids, see: E. Foresti, G. Palmieri, M. Petrini, R. Profeta, Org. Biomol. Chem. 2003, 1, 4275-4281.
6. a) A. S. Kende, J. S. Mendoza, Tetrahedron Lett. 1991, 32, 1699-1702;
7. b) M. A. Sturgess, D. J. Yarberry, Tetrahedron Lett. 1993, 34, 4743 -4747.
8. a) S. R. S. S. Kotti, C. Timmons, G. Li, Chem. Biol. Drug Des. 2006, 67, 101-114;
9. b) E. T. Michalson, J. Szmuszkovicz, Prog. Drug Res. 1989, 33, 135-149;
10. c) A. Viso, R. Fernandez de la Pradilla, A. Garcia, A. Flores, Chem. Rev. 2005, 105, 3167-3196;
11. d) P. Merino, A. Lanaspa, F. L. Merchan, T. Tejero, Tetrahedron: Asymmetry 1998, 9, 629-646.
12. Z. Zubovics, L. Toldy, A. Varro, G. Rablokzky, M. Kürthy, P. Dvortsak, G. Jerkovich, E. Tomori, Eur. J. Med. Chem. 1986, 21, 370-378.
13. J. Szmuszkovicz, P. F. Von Voigtlander, M. P. Kane, J. Med. Chem. 1981, 24, 1230-1236.
14. G. Szilagyi, E. Kasztreiner, P. Matyus, J. Kosary, K. Czako, G. Cseh, Z. Huszti, L. Tardos, E. Kosa, L. Jaszlits, Eur. J. Med. Chem. 1984, 19, 111-117.
15. J. Gonzalez-Sabin, V. Gotor, F. Rebolledo, Chem. Eur. J. 2004, 10, 5788-5794.
16. N. Mibu, K. Yokomizo, T. Miyata, K. Sumoto, Chem. Pharm. Bull. 2007, 55, 1406-1411.
17. O. Rebollo, E. Del Olmo, G. Ruiz, J. L. Lopez-Perez, A. Gimenez, A. San Feliciano, Bioorg. Med. Chem. Lett. 2008, 18, 184-187.
18. a) H.-U. Blaser, Chem. Rev. 1992, 92, 935-952;
19. b) K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833-856;
20. c) E. N. Jacobsen, in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, Weinheim, 1993, p. 159;
21. d) H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547;
22. e) J. M. Mitchell, N. S. Finney, Tetrahedron Lett. 2000, 41, 8431-8434;
23. f) D. Savoia, Top. Organomet. Chem. 2005, 15, 1-58.
24. a) Y. Sohtome, N. Takemura, R. Takagi, Y. Hashimoto, K. Nagasawa, Tetrahedron 2008, 64, 9423-9429;
25. b) L. Pignataro, M. Benaglia, M. Cinquini, F. Cozzi, G. Celentano, Chirality 2005, 17, 396-403.
26. a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. Int. Ed. 1998, 37, 2580-2627;
27. b) A. Viso, R. Fernandez de la Pradilla, Recent Res. Dev. Org. Chem. 2000, 4, 327-334;
28. c) E. T. Michalson, J. Szmuszkovicz, Prog. Drug Res. 1989, 33, 135-149.
29. a) F. P. Dwyer, F. L. Garvan, A. Shulman, J. Am. Chem. Soc. 1959, 81, 290-294;
30. b) R. G. Asperger, C. F. Liu, Inorg. Chem. 1965, 4, 1492-1494;
31. c) S. Pikul, E. J. Corey, Org. Synth. 1992, 71, 22-29;
32. d) K. Saigo, N. Kubota, S. Takebayashi, M. Hasegawa, Bull. Chem. Soc. Jpn. 1986, 59, 931-932;
33. e) E. J. Corey, D.-H. Lee, S. Sarshar, Tetrahedron: Asymmetry 1995, 6, 3-6;
34. f) I. Alfonso, C. Astorga, F. Rebolledo, V. Gotor, Chem. Commun. 1996, 2471-2472.
35. a) M. B. Gasc, A. Lattes, J. J. Perie, Tetrahedron 1983, 39, 703731;
36. b) D. Pini, A. Iuliano, C. Rosini, P. Salvadori, Synthesis 1990, 1023-1024;
37. c) G. Swift, D. Swern, J. Org. Chem. 1967, 32, 511-517;
38. d) N. Kalyanam, G. Venkateswara Rao, Tetrahedron Lett. 1993, 34, 1647-1648;
39. e) B. Baruah, D. Prajapati, J. S. Sandhu, Tetrahedron Lett. 1995, 36, 6747-6750;
40. f) H. Tanaka, H. Dhimane, H. Fujita, Y. Ikemoto, S. Torii, Tetrahedron Lett. 1988, 29, 3811-3814;
41. g) J. M. Aurrecoechea, A. Fernandez-Acebes, Tetrahedron Lett. 1992, 33, 4763-4766;
42. h) S. V. Pan- sare, M. G. Malusare, Tetrahedron Lett. 1996, 37, 2859-2862;
43. i) M. T. Reetz, R. Jaeger, R. Drewlies, M. Hubel, Angew. Chem. Int. Ed. Engl. 1991, 30, 103-106;
44. j) M. T. Reetz, D. Rohrig, K. Harms, G. Frenkling, Tetrahedron Lett. 1994, 35, 8765-8768;
45. k) A. Dondoni, F. L. Merchan, P. Merino, T. Tejero, V. Bertolasi, J. Chem. Soc., Chem. Commun. 1994, 1731-1733;
46. l) M. L. Morris, M. A. Sturgess, Tetrahedron Lett. 1993, 34, 43-46;
47. m) P. Merino, A. Lanaspa, F. L. Merchan, T. Tejero, Tetrahedron: Asymmetry 1997, 8, 2381-2401.
48. H. H. Baer, L. Urbas, in The Chemistry of the Nitro and Nitroso Groups, Part 2 (Ed.: S. Patai), Interscience, New York, 1970, p. 117.
49. H. Adams, J. C. Anderson, S. Peace, A. M. K. Pennell, J. Org. Chem. 1998, 63, 9932-9934.
50. In this review we use the syn/anti nomenclature according to the Masamune convention (see S. Masamune, S. A. Ali, D. L. Snitman, D. S. Garvey, Angew. Chem. Int. Ed. Engl. 1980, 19, 557-558 and S. Masamune, T. Kaiho, D. S. Garvey, J. Am. Chem. Soc. 1982, 104, 5521-5523): that is, considering the amino and nitro functionalities as the substituents of the carbon chain oriented in a zigzag disposition. Other dispositions, used in some cases in the original publications cited here, lead to misunderstanding of the relative configuration and should be avoided. Diastereoselectivities are indicated as diastereomeric ratios in the form of dr, as recommended for stereoselective reactions in which at least two isomers can be obtained. For an excellent and comprehensive discussion on the terminology used in stereochemistry see: G. Helmchen, in Stereoselective Synthesis, Houben-Weyl (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1996, vol. 1, p. 1.
51. a) N. Kise, K. Kashiwagi, M. Watanabe, J. Yoshida, J. Org. Chem. 1996, 61, 428-429;
52. b) Y. S. Park, M. L. Boys, P. Beak, J. Am. Chem. Soc. 1996, 118, 3757-3758.
53. J. C. Anderson, S. Peace, S. Pih, Synlett 2000, 850-852.
54. C. Qian, F. Gao, R. Chen, Tetrahedron Lett. 2001, 42, 4673.
55. K.-i. Yamada, S. J. Harwood, H. Groger, M. Shibasaki, Angew. Chem. Int. Ed. 1999, 38, 3504-3506.
56. P. Merino, E. Marques-Lopez, R. P. Herrera, Adv. Synth. Catal. 2008, 350, 1195-1208.
57. K. Yamada, G. Moll, M. Shibasaki, Synlett 2001, 980-982.
58. N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. J0rgensen, Angew. Chem. Int. Ed. 2001, 40, 2992-2995.
59. K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. J0rgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844.
60. J. C. Anderson, G. P. Howell, R. M. Lawrence, C. S. Wilson, J. Org. Chem. 2005, 70, 5665-5670.
61. M. A. Sturgess, D. J. Yarberry, Tetrahedron Lett. 1993, 34, 4743-4746.
62. K. R. Knudsen, K. A. J0rgensen, Org. Biomol. Chem. 2005, 3, 1362-1364.
63. C. Palomo, M. Oiarbide, A. Laso, Angew. Chem. Int. Ed. 2005, 44, 3881-3884.
64. C. Palomo, M. Oiarbide, R. Halder, A. Laso, R. Lopez, Angew. Chem. Int. Ed. 2006, 45, 117-120.
65. P. H. O'Brien, D. R. Sliskovic, C. J. Blankley, B. Roth, M. W Wilson, K. L. Hamelehle, B. R. Krause, R. L. Stanfield, J. Med. Chem. 1994, 37, 1810-1822.
66. C. Matt, A. Wagner, C. Mioskowski, J. Org. Chem. 1997, 62, 234-235.
67. H. Zhou, D. Peng, B. Qin, Z. Hou, X. Liu, X. Feng, J. Org. Chem. 2007, 72, 10302-10304.
68. a) R. G. Pearson, J. Am. Chem. Soc. 1963, 85, 3533-3539;
69. b) R. J. Balahura, R. B. Jordan, J. Am. Chem. Soc. 1970, 92, 1533-1539.
70. According to the experimental results and ESI-HRMS and 1H NMR studies of 36-CuI, the authors speculated that complex A should be the active species. For more details of discussion and the proposed transition state model, see the Supporting Information of the original publication 9 (ref. 35).
71. C. Tan, X. Liu, L. Wang, J. Wang, X. Feng, Org. Lett. 2008, 10, 5305-5308.
72. B. M. Trost, D. W. Lupton, Org. Lett. 2007, 9, 2023-2026.
73. F. Gao, J. Zhu, Y. Tang, M. Deng, C. Qian, Chirality 2006 18, 741 -745.
74. Z. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 2170-2171.
75. S. Handa, V. Gnanadesikan, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 4900-4901.
76. a) A. Berkessel, H. Groger, Asymmetric Organocatalysis, Wiley- VCH, Weinheim, 2005;
77. b)P.I.Dalko, Enantioselective Organocatalysis: Reaction and Experimental Procedures, John Wiley & Sons, New York, 2007.
78. T. Okino, S. Nakamura, T. Furukawa, Y. Takemoto, Org. Lett. 2004, 6, 625-627.
79. a) F. G. Bordwell, G. Ji, J. Am. Chem. Soc. 1991, 113, 8398-8401;
80. b) M. C. Etter, Z. Urbanczyk-Lipkowska, M. Zia-Ebrah- imi, T.W. Panunto, J. Am. Chem. Soc. 1990, 112, 8415-8426;
81. c) T. R. Kelly, M. H. Kim, J. Am. Chem. Soc. 1994, 116, 7072-7080.
82. a) Y. Takemoto, Org. Biomol. Chem. 2005, 3, 4299-4306;
83. b) Y. Takemoto, H. Miyabe, Chimia 2007, 61, 269-275;
84. c) Y. Takemoto, J. Synth. Org. Chem. Jpn. 2006, 64, 1139-1147;
85. d) S.J. Connon, Chem. Eur. J. 2006, 12, 5418-5427
86. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673.
87. X. Xu, T. Furukawa, T. Okino, H. Miyabe, Y. Takemoto, Chem. Eur. J. 2006, 12, 466-476.
88. B. M. Nugent, R. A. Yoder, J. N. Johnston, J. Am. Chem. Soc. 2004, 126, 3418-3419.
89. A. Singh, J. N. Johnston, J. Am. Chem. Soc. 2008, 130, 5866-5867.
90. B. Shen, J. N. Johnston, Org. Lett. 2008, 10, 4397-4400.
91. D. Uraguchi, K. Koshimoto, T. Ooi, J. Am. Chem. Soc. 2008, 130, 10878-10879.
92. T. P. Yoon, E. N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, 466-468.
93. C. Rampalakos, W. D. Wulff, Adv. Synth. Catal. 2008, 350, 1785 -1790.
94. T. Mecozzi, M. Petrini, Synlett 2000, 73-74.
95. F. Fini, V. Sgarzani, D. Pettersen, R. P. Herrera, L. Bernardi, A. Ricci, Angew. Chem. Int. Ed. 2005, 44, 7975-7978.
96. C. Palomo, M. Oiarbide, A. Laso, R. Lopez, J. Am. Chem. Soc. 2005, 127, 17622-17623.
97. E. Gomez-Bengoa, A. Linde, R. Lopez, I. Mugica-Mendiola, M. Oiarbide, C. Palomo, J. Am. Chem. Soc. 2008, 130, 7955-7966.
98. L. Bernardi, F. Fini, R. P. Herrera, A. Ricci, V. Sgarzani, Tetrahedron 2006, 62, 375-380.
99. C. M. Bode, A. Ting, S. E. Schaus, Tetrahedron 2006, 62, 11499-11505.
100. M. T. Robak, M. Trincado, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 15110-15111.
101. Y.-W. Chang, J.-J. Yang, J.-N. Dang, Y.-X. Xue, Synlett 2007, 2283-2285.
102. C. Wang, Z. Zhou, C. Tang, Org. Lett. 2008, 10, 1707-1710.
103. B. Han, Q.-P. Liu, R. Li, X. Tian, X.-F. Xiong, J.-G. Deng, Y.- C. Chen, Chem. Eur. J. 2008, 14, 8094-8097.
104. C.-J. Wang, X.-Q. Dong, Z.-H. Zhang, Z.-Y. Xue, H.-L. Teng, J. Am. Chem. Soc. 2008, 130, 8606-8607.
105. M. Rueping, A. P. Antonchick, Org. Lett. 2008, 10, 1731-1734.
106. C. Rampalakos, W. D. Wulff, Adv. Synth. Catal. 2008, 350, 1785 -1790.
107. J. C. Anderson, A. J. Blake, G. P. Howell, C. Wilson, J. Org. Chem. 2005, 70, 549-555.
108. L. Wang, C. Tan, X. Liu, X. Feng, Synlett 2008, 2075-2077.
109. J.-L. Garcfa-Ruano, M. Topp, J. Lopez-Cantarero, J. Aleman, M. J. Remuifian, M. B. Cid, Org. Lett. 2005, 7, 4407-4410.
110. N. K. Pahadi, H. Ube, M. Terada, Tetrahedron Lett. 2007, 48, 8700-8703.