N-heterocyclic carbene: A versatile organocatalyst

Chinese Journal of Organic Chemistry

Volumn 26, Issue 6, 2006, Pages 745-756

  Sun, Xiao Yu ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

N heterocyclic carbene; Organocatalyst; Stetter reaction; Umpolung reaction

Indexed keywords

EID: 33746322880     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (108)

1. (a) Arduengo III, A. J.; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1991, 113, 361.
2. (b) Arduengo III, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1992, 114, 5530.
3. (a) Wanzlick, H.-W. Angew. Chem. 1962, 74, 129;
4. Angew. Chem., Int. Ed. Engl. 1962, 1, 75.
5. (b) Wanzlick, H.-W.; SchKnherr, H.-J. Justus Liebigs Ann. Chem. 1970, 731, 176.
6. Arduengo III, A. J.; Davidson, F.; Dias, H. V. R.; Goerlich, J. R.; Khasnis, D.; Marshall, W. J.; Prakasha, T. K. J. Am. Chem. Soc. 1997, 119, 12742.
7. Cole, M. L.; Jones, C.; Junk, P. C. New J. Chem. 2002, 26, 1296.
8. Arduengo III, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. K. J. Am. Chem. Soc. 1992, 114, 5530.
9. Herrmann, W. A.; Köcher, C.; Goossen, L.; Artus, G. R. Chem. Eur. J. 1996, 2, 1627.
10. (a) Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. Chem. Eur. J. 1996, 2, 772;
11. (b) Dias, H. V. R.; Jin, W. Tetrahedron Lett. 1994, 35, 1365.
12. Enders, K. D.; Breuer, J.; Raabe, J.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Brode, S. Angew. Chem. 1995, 107, 1119;
13. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
14. Füstner, A.; Krause, H.; Ackermann, L.; Lehmann, C. W. Chem. Commun. 2001, 2240.
15. (a) Alcarazo, M.; Roseblade, S. J.; Alonso, E.; Fernández, R.; Alvarez, E.; Lahoz, F. J.; Lassaletta, J. M. J. Am. Chem. Soc. 2004, 126, 13242.
16. (b) Nyce, G. W.; Csihony, S.; Waymouth, R. M.; Hedrick, J. L. Chem. Eur. J. 2004, 10, 4073.
17. (c) Pesch, J.; Harms, K.; Bach, T. Eur. J. Org. Chem. 2004, 2025.
18. Otto, M.; Conejero, S.; Canac, Y.; Romanenk, V. D.; Rudzevitch, V.; Bertrand, G. J. Am. Chem. Soc. 2004, 126, 1016.
19. (a) Despagnet-Ayoub, E.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126, 10198.
20. (b) Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J. Am. Chem. Soc. 2004, 126, 4366.
21. For reviews on N-heterocyclic carbenes, see: (a) Herrmann, W. A. Angew. Chem. 2002, 114, 1342;
22. Angew. Chem., Int. Ed. 2002, 41, 1291.
23. (b) Herrmann, W. A.; Köcher, C. Angew. Chem. 1997, 109, 2256;
24. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
25. (c) Arduengo III, A. J.; Krafczyk, R. Chem. Unserer Zeit 1998, 32, 6.
26. (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
27. (a) Raabe, G.; Breuer, K.; Enders, D.; Teles, J. H. T. Z. Naturforsch. 1996, 17a, 95.
28. (b) Enders, D.; Breuer, K.; Teles, J. H.; Runsink, J. Liebig. Ann. Chem. 1996, 2019.
29. (c) Enders, D.; Breuer, K.; Teles, J. H.; Ebel, K. J. Prakt. Chem. 1997, 339, 397.
30. (d) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
31. Duong, H. A.; Tekavec, T. N.; Arif, A. M.; Louie, J. Chem. Commun. 2004, 112.
32. Rigby, J. H.; Wang, Z. Q. Org. Lett. 2002, 4, 4289.
33. (a) Nair, V.; Bindu, S.; Sreekumar, V.; Rath, N. P. Org. Lett. 2003, 5, 665.
34. (b) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
35. (c) Fei, Z.-F.; Zhao, D.-B.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J. Chem. Eur. J. 2004, 10, 4886.
36. (d) Nair, V.; Sreekumar, V.; Bindu, S.; Suresh, E. Org. Lett. 2005, 7, 2297.
37. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
38. Wöhler, F.; Liebig, J. Ann. Pharm. 1832, 3, 249.
39. Lapworth, A. J. Chem. Soc. 1903, 83, 995.
40. Seebach, D. Angew. Chem. 1979, 91, 259;
41. Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
42. Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 296.
43. Mizuhara, S.; Handler, P. J. Am. Chem. Soc. 1954, 76, 571.
44. Sheehan, J.; Hunnemann, D. H. J. Am. Chem. Soc. 1966, 88, 3666.
45. Dvorak, C. A.; Rawal, V. H. Tetrahedron Lett. 1998, 39, 2925.
46. Tagaki, W.; Tamura, Y.; Yano, Y. Bull. Chem. Soc. Jpn. 1980, 53, 478.
47. Zhao, C.; Chen, S.; Wu, P.; Wen, Z. Acta. Chim. Sinica 1988, 46, 784 (in Chinese).
48. Marti, J.; Castells, J.; López, C. F. Tetrahedron Lett. 1993, 34, 521.
49. (a) Breuer, K. Ph.D. Dissertation, Technical University of Aachen, Aachen, Germany, 1997.
50. (b) Enders, D.; Breuer, K.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1217.
51. (c) Enders, D.; Breuer, K. Comprehensive Asymmetric Catalysis, Vol. 3, Springer-Verlag, Heidelberg, 1999, 1093.
52. (d) Teles, J. H.; Breuer, K.; Enders, D.; Gielen, H. Synth. Commun. 1999, 29, 1.
53. Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743.
54. (a) Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407.
55. (b) Stetter, H. Angew. Chem. 1976, 88, 695;
56. Angew. Chem., Int. Ed. Engl. 1976, 15, 639.
57. (a) Tiebes, J. Diploma Thesis, Technical University of Aachen, Aachen, Germany, 1990.
58. (b) Enders, D. In Stereoselective Synthesis, Eds.: Ottow, E.; Schoellkopf, K.; Schulz, B.-G., Springer-Verlag, Berlin-Heidelberg, 1994, pp. 63-90.
59. (c) Enders, D.; Bockstiegel, B.; Dyker, H.; Jegelka, U.; Kipphardt, H.; Kownatka, D.; Kuhlmann, H.; Mannes, D.; Tiebes, J.; Papadopoulos, K., Dechema-Monographies, VCH, Weinheim, 1993, 129, 209.
60. Yadav, J. S.; Anuradha, K.; Subba Reddy, B. V.; Eeshwaraiah, B. Tetrahedron Lett. 2003, 50, 8959.
61. Raghavan, S.; Anuradha, K. Tetrahedron Lett. 2002, 43, 5181.
62. Enders, D.; Breuer, K.; Teles, J. H.; Runsink, J. Liebigs Ann. Chem. 1996, 2019.
63. Ciganek, E. Synthesis 1995, 1311.
64. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899.
65. (a) Kerr, M. S.; Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.
66. (b) Kerr, M. S.; Rovis, T. 19th International Congress of Heterocyclic Chemistry, Fort Collins, Colorado, 2003, 14-PO-289.
67. (c) Readde Alaniz, J.; Rovis, T. 19th International Congress of Heterocyclic Chemistry, Fort Collins, Colorado, 2003, 14-PO-291.
68. (d) Reynolds, N. T.; Rovis, T. 19th International Congress of Heterocyclic Chemistry, Fort Collins, Colorado, 2003, 14-PO-292.
69. Kerr, M. S.; Rovis, T. Synlett 2003, 1934.
70. Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876.
71. Readde Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 6284.
72. Nakamura, T.; Hara, O.; Tamura, T.; Makino, K.; Hamada, Y. Synlett 2004, 155.
73. Mennen, S. M.; Gipson, J. D.; Kim, Y. R.; Miller, S. J. J. Am. Chem. Soc. 2005, 127, 1654.
74. (a) Mattson, A. E.; Bharadwaj, A. R.; Scheldt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
75. (b) Bharadwaj, A. R.; Scheldt, K. A. Org. Lett. 2004, 6, 2465.
76. Harrington, P. E.; Tius, M. A. Org. Lett. 1999, 1, 649.
77. Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 723, 9696.
78. Mattson, A. E.; Scheldt, K. A. Org. Lett. 2004, 6, 4363.
79. Burstein, C.; Glorius, R. Angew. Chem., Int. Ed. 2004, 43, 6205.
80. Hüning, S.; Wehner, G. Chem. Ber. 1979, 112, 2062.
81. Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5288.
82. (a) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432.
83. (b) Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326.
84. Enders, D.; Niemeier, O. Synlett 2004, 2111.
85. Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905.
86. Chow, Y.-K. K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126.
87. Reynolds, N. T.; Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518.
88. (a) Suzuki, Y.; Toyota, T.; Imada, F.; Sato, M.; Miyashita, A. Chem. Commun. 2003, 1314.
89. (b) Miyashita, A.; Suzuki, K.; Iwamoto, E. O.; Higashino, T. Heterocycles 1998, 49, 405.
90. (c) Miyashita, A.; Suzuki, A.; Iwamoto, E. O.; Higashino, T. Chem. Pharm. Bull. 1998, 46, 390.
91. (a) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583.
92. (b) Grasa, G. A.; Güveli, T.; Singh, R.; Nolan, S. P. J. Org. Chem. 2003, 68, 2812.
93. (c) Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587.
94. (d) Singh, R.; Kissling, R. M.; Letellier, M.-A.; Nolan, S. P. J. Org. Chem. 2004, 69, 209.
95. (a) Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770.
96. (b) Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347.
97. For example: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 4243.
98. (b) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
99. (c) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370.
100. (d) Fu, G. C. Acc. Chem. Res. 2000, 33, 412.
101. (e) Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234.
102. (f) Tao, B.; Lo, M. C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 353.
103. (g) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430.
104. (h) Vedejs, E.; Rozners, E. J. Am. Chem. Soc. 2001, 123, 2428.
105. Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914.
106. Duong, H. A.; Cross, M. J.; Louie, J. Org. Lett. 2004, 6, 4679.
107. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
108. Song, J. J.; Tan, Z.; Reeves, J. T.; Gallou, F.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2005, 7, 2193.