Progress in preparation of chiral NHC-metal complexes and their use as catalysts in asymmetric reactions

Chinese Journal of Organic Chemistry

Volumn 29, Issue 10, 2009, Pages 1499-1507

  Gu, Lina ^a,b   Zhu, Guanbin ^a   Song, Haibin ^a   Zi, Guofu ^b  

^a NANKAI UNIVERSITY   (China)

^b BEIJING NORMAL UNIVERSITY   (China)

Author keywords

Chiral NHC metal complex; Enantioselective catalysis; Synthesis

Indexed keywords

EID: 73849102905     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (61)

1. Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds, John Wiley and Sons, New York, 1988.
2. Duncan, A. P.; Bergman, R. G. Chem. Record2002, 2, 431.
3. Mountford, P. Chem. Commun. 1997, 2127.
4. Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565.
5. Schrock, R. R. Chem. Rev. 2002, 102, 145.
6. Zi, G.-F.; Zhang, Z.-B.; Xiang, L.; Wang, Q.-W. Chin. J. Org. Chem. 2006, 26, 1606 (in Chinese).
7. For reviews see: (a) Schrock, R. R.; Hoveyda, A. H. Angew, Chem., Int. Ed. 2003, 42, 4592.
8. (b) Schrock, R. R. Tetrahedron 1999, 55, 8141.
9. (c) Zhu, J.; Zhang, X.-J.; Zou, Y. Chin. J. Org. Chem. 2004, 24, 127 (in Chinese).
10. (d) Li, R.-Q.; Fu, Y.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 1004 (in Chinese).
11. (e) Guo, Y.-C.; Xiao, W.-J. Chin. J. Org. Chem. 2005, 25, 1334 (in Chinese).
12. (f) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
13. (g) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181.
14. (h) Bourrissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
15. (i) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. 1997, 36, 2162.
16. (j) Glorius, F. N-Heterocyclic Carbenes in Transition Metal Catalysis (Topics in Organometallic Chemistry), Springer, Berlin, Heidelberg, 2007.
17. (k) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 53, 619.
18. Herrmann, W. A.; Goossen, L. J.; Köcher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805.
19. Herrmann, W. A.; Goossen, L. J.; Artus, G. R. J.; Köcher, C. Organometallics 1997, 16, 2472.
20. Arduengo, A. J.; Krafczyk, R.; Schmutzler, R. Tetrahedron 1999, 55, 14523.
21. Suzuki, Y.; Muramatsu, K.; Yamauchi, K.; Morie, Y.; Sato, M. Tetrahedron 2006, 62, 302.
22. Herrmann, W. A.; K6cher, C.; Goossen, L. J.; Artus, G. R. J. Chem. Eur. J. 1996, 2, 1627.
23. Powell, M. T.; Hou, D.; Perry, M. C.; Cui, X.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 8878.
24. Perry, M. C.; Cui, X.; Powell, M. T.; Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 113.
25. Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162.
26. Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
27. Gade, L. H.; César, V.; Bellemin-Laponnaz, S. Angew. Chem., Int. Ed. 2004, 43, 1014.
28. Clyne, D. S.; Jin, J.; Genest, E.; Galluci, J. C.; RajanBabu, T. V. Org. Lett. 2000, 2, 1125.
29. Bolm, C.; Kesselgruber, M.; Raabe, G. Organometallics 2002, 21, 707.
30. Huang, J.; Jafarpour, L.; Hillier, A. C.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 2878.
31. Perry, M. C.; Cui, X.; Burgess, K. Tetrahedron: Asymmetry 2002, 13, 1969.
32. Alcarazo, M.; Roseblsde, S. J.; Alonso, E.; Fernández, R.; Alvarez, E.; Laboz, F. J.; Lassaletta, J. M. J. Am. Chem. Soc. 2004, 126, 13242.
33. Winn, C. L.; Guillen, F.; Pytkowicz, J.; Roland, S.; Mangeney, P.; Alexakis, A. J. Organomet. Chem. 2005, 690, 5672.
34. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
35. Seiders, R. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 5, 3225.
36. Veldhuizen, J. J. V.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
37. Bappert, E.; Helmchem, G. Synlett., 2004, 1789.
38. Chianese, A. R.; Li, X.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics 2003, 22, 1663.
39. Zinner, S. C.; Herrmann, W. A.; Kühn, F. E. J. Organomet. Chem. 2008, 695, 1543.
40. Zinner, S. C.; Herrmann, W. A.; Kühn, F. E. Tetrahedron: Asymmetry 2008, 19, 1532.
41. Rivas, F. M.; Riaz, U.; Gieessert, A.; Smulik, J. A.; Diver, S. T. Org. Lett. 2001, 3, 2673.
42. Rivas, F. M.; Gieessert, A.; Diver, S. T. J. Org. Chem. 2002, 67, 1708.
43. Duan, W.; Shi, M.; Rong, G. Chem. Commun. 2003, 2916.
44. Xu, Q.; Gu, X.; Liu, S.; Dou, Q.; Shi, M. J. Org. Chem. 2007, 72, 2240.
45. (a) Chen, T.; Jiang, J.-J.; Xu, Q.; Shi, M. Org. Lett. 2007, 9, 865.
46. (b) Zhang, T.; Shi, M. Chem. Eur. J. 2008, 14, 3759.
47. (c) Ma, G.-N.; Zhang, T.; Shi, M. Org. Lett. 2009, 11, 875.
48. (d) Zhang, T.; Wang, W.; Gu, X.; Shi, M. Organometallics 2008, 27, 753.
49. (e) Liu, Z.; Zhang, T.; Shi, M. Organometallics 2008, 27, 2668.
50. Song, H.; Gu, L.-N.; Zi, G. J. Organomet. Chem. 2009, 694, 1493.
51. Enders, D.; Gielen, H. J. Organomet. Chem. 2001, 617-618, 70.
52. Alexakis, A.; Winn, C. L.; Guillen, F.; Pytkowicz, J.; Roland, S.; Mangeney, P. Adv. Synth. Catal. 2003, 345, 345.
53. Guillen, F.; Winn, C. L.; Alexakis, A. Tetrahedron: Asymmetry 2001, 12, 2083.
54. Chianese, A. R.; Crabtree, R. H. Organometallics 2005, 24, 4432.
55. Enders, D.; Gielen, H.; Breuer, K. Tetrahedron: Asymmetry 1997, 8, 3571.
56. Faller, J. W.; Fontaine, P. P. Organometallics 2006, 25, 5887.
57. Seo, H.; Kim, B. Y.; Lee, J. H.; Park, H.; Son, S. U.; Chung, Y. K. Organometallics 2003, 22, 4783.
58. Seo, H.; Park, H.-J.; Kim, B. Y.; Lee, J. H.; Son, S. U.; Chung, Y. K. Organometallics 2003, 22, 618.
59. Veldhuizen, J. J. V.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502.
60. Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402.
61. Bonnet, L. G.; Douthwaite, R. E. Organometallics 2003, 22, 4187.