Chiral guanidine catalyzed enantioselective reactions

Chemistry - An Asian Journal

Volumn 4, Issue 4, 2009, Pages 488-507

  Leow, Dasheng ^a   Tan, Choon Hong ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Asymmetric catalysis; Br nsted bases; Guanidines; Hydrogen bonding; Organocatalysis

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYTIC ACTIVITY; ENANTIOSELECTIVE REACTIONS; GUANIDINES; HYDROGEN BONDING; HYDROGEN BONDINGS; ORGANOCATALYSIS;

CATALYSTS; ENANTIOSELECTIVITY; HYDROGEN; HYDROGEN BONDS; RATE CONSTANTS; REACTION KINETICS; SELF ASSEMBLY;

CATALYSIS;

GUANIDINE DERIVATIVE;

CATALYSIS; CHEMICAL MODEL; CHEMISTRY; HYDROGEN BOND; REVIEW; STEREOISOMERISM;

CATALYSIS; GUANIDINES; HYDROGEN BONDING; MODELS, CHEMICAL; STEREOISOMERISM;

EID: 66149095568     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800361     Document Type: Review

References (102)

1. a) R. G. S. Berlinck, M. H. Kossuga, Nat. Prod. Rep. 2005, 22, 516-550;
2. b) R. G. S. Berlinck, A. C. B. Burtoloso, M. H. Kossuga, Nat. Prod. Rep. 2008, 25, 919-954.
3. a) C. L. Hannon, E. V. Anslyn in Bioorganic Chemistry Frontiers, Vol. 3 (Ed.: H. Dugas), Springer-Verlag, Berlin, Heidelberg, 1993, pp. 193-256;
4. b) Y. Yamamoto, S. Kojima in The Chemistry of Amidines and Imidates, Vol. 2 (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1991, pp. 485-526.
5. For reviews on guanidium-based anionic receptors, see: a) M. D. Best, S. L. Tobey, E. V. Anslyn, Coord. Chem. Rev. 2003, 240, 3-15;
6. b) K. A. Schng, W. Lindner, Chem. Rev. 2005, 105, 67-113;
7. c) P. Blondeau, M. Segura, R. P. Fernandez, J. de Mendoza, Chem. Soc. Rev. 2007, 36,198-210.
8. For review on application of guanidines in organic synthesis, see: T. Ishikawa, T. Kumamoto, Synthesis 2006, 737-752.
9. For an extensive review on asymmetric catalysis using hydrogen bonding, see: A. G. Doyle, E.N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743.
10. For personal research accounts, see: a) T. Ishikawa, T. Isobe, Chem. Eur. J. 2002, 8, 552-557;
11. b) K. Nagasawa, Y. Hashimoto, Chem. Rec. 2003, 3, 201-211;
12. c) T. Ishikawa, ARKIVOC 2006,148-168.
13. For reviews on asymmetric Henry reactions, see: a) C. Palomo, M. Oiarbide, A. Mielgo, Angew. Chem. 2004, 116, 5558-5560; Angew. Chem. Int. Ed. 2004, 43, 5442-5444;
14. b) J. Boruwa, N Gogoi, P.P. Saikia, N C. Barua, Tetrahedron: Asymmetry 2006, 17, 3315-3326;
15. c) C. Palomo, M. Oiarbide, A. Laso, Eur. J. Org. Chem. 2007, 2561-2574.
16. a) P. H. Boyle, M. A. Convery, A. P. Davis, G. D. Hosken, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 239-242;
17. b) E. va-n Aken, H. Wynberg, F. van Bolhuis, J. Chem. Soc. Chem. Commun. 1992, 629-630.
18. R. Chinchilla, C. Najera, P. Sánchez-Agullo, Tetrahedron: Asymmetry 1994, 5,1393-1402.
19. D. Ma, Q. Pan, F. Han, Tetrahedron Lett. 2002, 43, 9401-9403.
20. a) A. Howard-Jones, P. J. Murphy, D. A. Thomas, J. Org. Chem. 1999, 64, 1039-1041;
21. b) M. T. Allingham; A. Howard-Jones, P.J. Murphy, D. A. Thomas, P. W. R. Caulkett, Tetrahedron Lett. 2003, 44, 8677-8680;
22. A. Howard-Jones, P.J. Murphy, D. A. Thomas, P. W. R. Caulkett, Tetrahedron Lett. 2003, 44, 8677-8680.
23. a) Y Sohtome, Y Hashimoto, K. Nagasawa, Adv. Synth. Catal. 2005, 347, 1643-1648;
24. b) Y Sohtome, N. Takemura, T. Iguchi, Y Hashimoto, K. Nagasawa, Synlett 2006,144-146;
25. c) Y Sohtome, Y Hashimoto, K. Nagasawa, Eur. J. Org. Chem. 2006, 2894-2897;
26. d) Y Sohtome, N. Takemura, K. Takada, R. Takagi, T. Iguchi, K. Nagasawa, Chem. Asian J. 2007, 2,1150-1160.
27. K. Takada, N. Takemura, K. Cho, Y Sohtome, K. Nagasawa, Tetrahedron Lett. 2008, 49,1623-1626.
28. A. P. Davis, K. J. Dempsey, Tetrahedron: Asymmetry 1995, 6, 2829-2840.
29. S. B. Tsogoeva, S. B. Jagtap, Z. A. Ardemasova, V. N Kalikhevich, Eur. J. Org. Chem. 2004, 4014-4019.
30. W. Ye, D. Leow, S. L. M. Goh, C.-T Tan, C.-H. Chian, C.-H. Tan, Tetrahedron Lett. 2006, 47, 1007-1010.
31. a) E. J. Corey, M.J. Grogan, Org. Lett. 1999, 1, 157-160;
32. b) T. Isobe, K. Fukuda, K. Yamaguchi, H. Seki, T. Tokunaga, T. Ishikawa, J. Org. Chem. 2000, 65, 7779-7785.
33. For reviews on organocatalytic asymmetric Michael reactions, see: D. Almaşi, D. A. Alonso, C. Násjera, Tetrahedron: Asymmetry 2007, 18, 299-365.
34. D. Ma, K. Cheng, Tetrahedron: Asymmetry 1999,10, 713-719.
35. B. Peng, K.-J. Cheng, D. Ma, Chin. J. Chem. 2000,18, 411-413.
36. Q.-B. Pan, D.-W. Ma, Chin. J. Chem. 2003, 21, 793-796.
37. a) T. Ishikawa, Y. Araki, T. Kumamoto, H. Seki, K. Fukuda, T. Isobe, Chem. Commun. 2001, 245-246;
38. b) A. Ryoda, N Yajima, T. Haga, T. Kumamoto, W. Nakanishi, M. Kawahata, K. Yamaguchi, T. Ishikawa, J. Org. Chem. 2008, 73, 133-141.
39. T. Kumamoto, K. Ebine, M. Endo, Y. Araki, Y Fushimi, I. Miyamoto, T. Ishikawa, T. Isobe, K. Fukuda, Heterocycles 2005, 66, 347-359.
40. M. Terada, H. Ube, Y Yaguchi, J. Am. Chem. Soc. 2006,128, 1454-1455.
41. For review on peptide catalysis, see: E. A. C. Davie, S. M. Mennen, Y Xu, S. J. Miller, Chem. Rev. 2007,107, 5759-5812.
42. B. R. Linton, M. H. Reutershan, C. M. Aderman, E. A. Richardson, K. R. Brownell, C. W. Ashley, C. A. Evans, S. J. Miller, Tetrahedron Lett. 2007, 48, 1993-1997.
43. J. Shen, T. T. Nguyen, Y.-P. Goh, W. Ye, X. Fu, J. Xu, C.-H. Tan, J. Am. Chem. Soc. 2006,128, 13692-13693.
44. a) W. Ye, J. Xu, C.-T. Tan, C.-H. Tan, Tetrahedron Lett. 2005, 46, 6875-6878;
45. b) Z. Jiang, W. Ye, Y Yang, C.-H. Tan, Adv. Synth. Catal. 2008, 350, 2345-2351;
46. c) W. Ye, Z. Jiang, Y Zhao, S. L. M. Goh, D. Leow, Y.-T Soh, C.-H. Tan, Adv. Synth. Catal. 2007, 349, 2454-2458.
47. For review on asymmetric aza-Michael reactions, see: L.-W. Xu, C-G. Xia, Eur. J. Org. Chem. 2005, 633-639.
48. a) V. Alcázar, J. R. Morán, J. de Mendoza, Tetrahedron Lett. 1995, 36, 3941-3944;
49. b) K. Nagasawa, A. Georgieva, H. Takahashi, T Nakata, Tetrahedron 2001, 57, 8959-8964;
50. c) M. Martín-Portugues, V. Alcazar, P. Prados, J. de Mendoza, Tetrahedron 2002, 58, 2951-2955.
51. For review on asymmetric syntheis of amino phosphonic acids, see: J.-A. Ma, Chem. Soc. Rev. 2006, 35, 630-636.
52. Z. Jiang, Y Zhang, W. Ye, C.-H. Tan, Tetrahedron Lett. 2007, 48, 51-54.
53. a) X. Fu, Z. Jiang, C.-H. Tan, Chem. Commun. 2007, 5058-5060;
54. b) M. Terada, T Ikehara, H. Ube, J. Am. Chem. Soc. 2007, 129, 14112-14113.
55. a) C F Nising, S. Brase, Chem. Soc. Rev. 2008, 37, 1218-1228;
56. b) N. Saito, A. Ryoda, W. Nakanishi, T Kumamoto, T Ishikawa, Eur. J. Org. Chem. 2008, 2759-2766.
57. For reviews on enantioselective protonation reactions, see: a) C Fehr, Angew. Chem. 1996, 108, 2726-2748;
58. Angew. Chem. Int. Ed. Engl. 1996, 35, 2566-2587;
59. b) A. Yanagisawa, K. Ishihara, H. Yamamoto, Synlett 1997, 411-420;
60. c) L. Duhamel, P. Duhamel, J.-C Plaquevent, Tetrahedron: Asymmetry 2004,15, 3653-3691.
61. D. Leow, S. Lin, S. K. Chittimalla, X. Fu, C.-H. Tan, Angew. Chem. 2008, 120, 5723-5727;
62. Angew. Chem. Int. Ed. 2008, 47, 5641-5645.
63. For reviews on asymmetric Diels-Alder reactions, see: a) E. J. Corey, Angew. Chem. 2002, 114, 1724-1741;
64. Angew. Chem. Int. Ed. 2002, 41, 1650-1667;
65. b) J. Shen, C.-H. Tan, Org. Biomol. Chem. 2008, 6, 3229-3236;
66. c) Y Wang, H. Li, Y.-Q. Wang, Y Liu, B. M. Foxman, L Deng, J. Am. Chem. Soc. 2007,129, 6364-6365.
67. a) F Recupero, C Punta, Chem. Rev. 2007, 107, 3800-3842;
68. b) J. Shen, C.-H. Tan, Org. Biomol. Chem. 2008, 6, 4096-4098.
69. M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044-16045.
70. For reviews on asymmetric nucleophilic epoxidations, see: A. Armstrong in Enantioselective Organocatalysis (Ed.: P. I. Dalko), Wiley- VCH, Weinheim, 2007, pp. 403-424.
71. a) T. Genski, G. Macdonald, X. Wei, N. Lewis, R. J. K. Taylor, ARKIVOC 2000, 266-273;
72. b) J. C. McManus, J. S. Carey, R. J. K. Taylor, Synlett 2003, 365-368;
73. c) J. C. McManus, T. Genski, J. S. Carey, R. J. K. Taylor, Synlett 2003, 369-371.
74. a) T. Kita, B. Shin, Y. Hashimoto, K. Nagasawa, Heterocycles 2007, 73, 241-247;
75. b) B. Shin, S. Tanaka, T. Kita, Y. Hashimoto, K. Nagasawa, Heterocycles 2008, 76, 801-810.
76. For recent reviews on asymmetric catalytic Mannich reactions, see: a) J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29-41;
77. b) A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797-5815.
78. S. Kobayashi, R. Yazaki, K. Seki, Y. Yamashita, Angew. Chem. 2008, 120, 5695-5697;
79. Angew. Chem. Int. Ed. 2008, 47, 5613-5615.
80. For reviews on asymmetric Strecker reactions, see: a) H. Gröger, Chem. Rev. 2003, 103, 2795-2827;
81. b) S. J. Connon, Angew. Chem. 2008, 120, 1194-1197;
82. Angew. Chem. Int. Ed. 2008, 47, 1176-1178.
83. a) M. S. Iyer, K. M. Gigstad, N. D. Namdev, M. Lipton, J. Am. Chem. Soc. 1996, 118, 4910-4911;
84. b) C. Becker, C. Hoben, D. Schollmeyer, G. Scherr, H. Kunz, Eur. J. Org. Chem. 2005, 1497-1499.
85. Y. Kitani, T. Kumamoto, T. Isobe, K. Fukuda, T. Ishikawa, Adv. Synth. Catal. 2005, 347, 1653-1658.
86. D. Basavaiah, K. V. Rao, B. S. Reddy, Tetrahedron: Asymmetry 2006, 17, 1036-1040.
87. T. Isobe, K. Fukuda, T. Ishikawa, Tetrahedron: Asymmetry 1998, 9, 1729-1735.
88. For reviews, see: Asymmetric Phase Transfer Catalysis (Ed.: K. Maruoka), Wiley-VCH, Weinheim, 2008.
89. T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956-2958;
90. Angew. Chem. Int. Ed. 2002, 41, 2832-2834.
91. T. Isobe, K. Fukuda, Y. Araki, T. Ishikawa, Chem. Commun. 2001, 243-244.
92. A. Hjelmencrantz, U. Berg, J. Org. Chem. 2002, 67, 3585-3594.
93. For reviews, see: a) The Claisen Rearrangement: Methods and Applications (Eds.: M. Hiersemann, U. Nubbemeyer), Wiley-VCH, Wein-heim, 2008;
94. b) K. C. Majumdar, S. Alam, B. Chattopadhyay, Tetrahedron 2008, 64, 597-643;
95. c) A. M. M. Castro, Chem. Rev. 2004, 104, 2939-3002.
96. C. Uyeda, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 9228-9229.
97. a) K. Hada, T. Watanabe, T. Isobe, T. Ishikawa, J. Am. Chem. Soc. 2001, 123, 7705-7706;
98. b) T. Haga, T. Ishikawa, Tetrahedron 2005, 61, 2857-2869;
99. c) D. Wannaporn, T. Ishikawa, M. Kawahata, K. Yamaguchi, J. Org. Chem. 2006, 71, 6600-6603.
100. D. Wannaporn, T. Ishikawa, Mol. Diversity 2005, 9, 321-331.
101. U. Köhn, M. Schulz, H. Görls, E. Anders, Tetrahedron: Asymmetry 2005, 16, 2125-2131.
102. N. Wu, H.-H. Wu, Y.-W. Jiang, Chin. J. Org. Chem. 2008, 28, 104-110.