Recent developments of chiral diaminocarbene-metal complexes for asymmetric catalysis

Current Organic Chemistry

Volumn 12, Issue 16, 2008, Pages 1370-1387

  Snead, David R ^a   Seo, Hwimin ^a   Hong, Sukwon ^a  

^a University of Florida ^*  (United States)

Author keywords

Asymmetric; Catalysis; Chiral; Diaminocarbene Metal; Ligands; N heterocyclic carbenes (NHCs); Olefin metathesis; Transition metal

Indexed keywords

CATALYSIS; COPPER COMPOUNDS; ENANTIOSELECTIVITY; METAL COMPLEXES; OLEFINS; PALLADIUM COMPOUNDS; TRANSITION METALS;

ASYMMETRIC; ASYMMETRIC CATALYSIS; CHIRAL; DIAMINOCARBENE-METAL; DIAMINOCARBENES; N-HETEROCYCLIC CARBENE; N-HETEROCYCLIC CARBENE LIGANDS; N-HETEROCYCLIC CARBENES; OLEFIN METATHESIS; TRANSITION-METAL-CATALYZED REACTIONS;

LIGANDS;

EID: 57649220770     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527208786241510     Document Type: Review

References (104)

1. Arduengo, A. J. III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc., 1991, 113, 361.
2. Clavier, H.; Nolan, S.P. Annu. Rep. Prog. Chem., 2007, 103, 193.
3. N-heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry, Springer-Verlag: New York, 2007, Vol. 21.
4. N-heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
5. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem. Int. Ed., 2007, 46, 2768.
6. Garrison, J. C.; Youngs, W. J. Chem. Rev., 2005, 105, 3978.
7. Peris, E. V.; Crabtree, R. H. Coord. Chem. Rev., 2004, 248, 2239.
8. Crudden, C. M.; Allen, D. P. Coord, Chem. Rev., 2004, 248, 2247.
9. Herrmann, W. A. Angew. Chem. Int, Ed., 2002, 41, 1290.
10. Alder, R. W. Diaminocarbenes: Exploring Structure and Reactivity. In Carbene Chemistry, from Fleeting Intermediates to Powerful Reagents; Bertrand, G. Ed.; Marcel Denker: New York, 2002, 153.
11. Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev., 2000, 100, 39.
12. Arduengo, A. J., III Acc. Chem. Res., 1999, 32, 913.
13. Green, J. C.; Scur, R. G.; Arnold, P. L.; Cloke, G. N. Chem. Commun., 1997, 1963.
14. Diez-Gonzalez, S.; Nolan, S. P. Coord. Chem. Rev., 2007, 251, 874.
15. Crabtree, R. H. J. Organomet. Chem., 2005, 690, 5451.
16. Alder, R. W.; Blake, M. E.; Chaker, L.; Harvey, J. N.; Paolini, F.; Schüitz, J. Angew. Chem. Int. Ed., 2004, 43, 5896.
17. Chianese, A.R.; Li, X.; Janzen, M. C.; Faller, J. W.; Crabtree, R. H. Organometallics, 2003, 22, 1663.
18. Chianese, A. R.; Kovacevic, A.; Zeglis, B. M.; Faller, J. W.; Crabtree, R. H. Organometallics, 2004, 23, 2461.
19. Rogers, M. M.; Stahl, S. S. N-Heterocyclic Carbenes as Ligands for High-Oxidation-State Metal Complexes and Oxidation Catalysis. In N-heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F. Ed.; Topics in Organometallic Chemistry, Springer Berlin: Heidelberg, 2007, Vol. 21, p. 21.
20. Kelly, R.A. III; Clavier, H.; Giudice, S.; Scott, N.M.; Stevens, E.D.; Bordner, J.; Samardjiev, I.; Hoff, C.D.; Cavallo, L.; Nolan, S.P. Organometallics, 2008, 27, 202.
21. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc., 2001, 123, 6543.
22. Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T. L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc., 2003, 125, 2546.
23. Herrmann, W. H.; Gooben, L. J.; Kocher, C.; Artus, G. R. J. Angew. Chem. Int. Ed., 1996, 35, 2805.
24. Perry, M. C.; Burgess, K. Tetrahedron Asymmetry, 2003, 14, 951.
25. Powell, M. T.; Hou, D. R.; Perry, M. C.; Cui, X.; Burgess, K. J. Am. Chem. Soc., 2001, 123, 8878.
26. Gade, L. H.; Bellemin-Laponnaz, S. Chiral N-Heterocyclic Carbenes as Stereodirecting Ligands in Asymmetric Catalysis. In N-heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F. Ed.; Topics in Organometallic Chemistry, Springer Berlin: Heidelberg, 2007, Vol. 21, 117.
27. Cesar, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev., 2004, 33, 619.
28. Mauduit, M.; Clavier, H. Asymmetric Catalysis with Metal-N-Heterocyclic Carbene Complexes. In N-Heterocyclic Carbenes in Synthesis, Nolan, S.P., Ed.; Wiley-VCH: Weinheim, 2006, 183.
29. Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett., 2001, 3, 3225.
30. Funk, T. W.; Berlin, J. M.; Grubbs, R. H. J. Am. Chem. Soc., 2006, 128, 1840.
31. Fournier, P. A.; Collins, S. K. Organometallics, 2007, 26, 2945.
32. Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc., 2002, 124, 4954.
33. Van Veldhuizen, J. J.; Campbell, J. E.; Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc., 2005, 127, 6877.
34. Giudici, I- E.; Hoveyda, A. H. J. Am. Chem. Soc., 2007, 129, 3824.
35. Berlin, J. M.; Goldberg, S. D.; Grubbs, R. H. Angew. Chem. Int. Ed., 2006, 45, 7591.
36. Song, C.; Ma, C.; Ma, Y.; Feng, W.; Ma, S.; Chai, Q.; Andrus, M. A. Tetrahedron Lett., 2005, 46, 3241.
37. Duan, W. L.; Shi, M.; Rong, G. B. Chem. Commun., 2003, 2916.
38. Gade, L. H.; Cesar, V.; Bellemin-Laponnaz, S. Angew. Chem. Int. Ed., 2004, 43, 1014.
39. Cesar, V.; Bellemin-Laponnaz, S.; Wadepohl, H.; Gade, L. H. Chem. Eur. J., 2005, 11, 2862.
40. Xu, Q.; Gu, X.; Liu, S.; Don, Q.; Shi M. J. Org. Chem., 2007, 72, 2240.
41. Faller, J. W.; Fontaine, P. P. Organometallics, 2006, 25, 5887.
42. Herrmann, W. A.; Baskakov, D.; Herdtweck, E.; Hoffmann, S. D.; Bunlaksananusom, T.; Rampf, F.; Rodefeld, L. Organometallics, 2006, 25, 2449.
43. Yuan, Y.; Raabe, G.; Bolm, C. J. Organomet. Chem., 2005, 690, 5747.
44. Enders, D.; Gielen, H.; Runsink, J.; Breuer, K.; Brode, S.; Boehn, K. Eur. J. Inorg. Chem., 1998, 913.
45. Focken, T.; Rudolph, J.; Bolm, C. Synthesis, 2005, 3, 429.
46. Arao, T.; Sato, K.; Kondo, K.; Aoyama, T. Chem. Pharm. Bull., 2006, 54, 1576.
47. Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. B. Angew. Chem. Int. Ed., 2003, 42, 5871.
48. Becht, J.; Bappert, E.; Helmchen, G. Adv. Synth. Catal., 2005, 347, 1495.
49. Bappert, E.; Helmchen, G. Synlett, 2004, 1789.
50. Crabtree, R. H.; Felkin, H.; Morris. G. E. J. Organomet. Chem., 1977, 141, 205.
51. Crabtree, R. H. Acc. Chem. Res., 1979, 12, 331.
52. Cui, X.; Burgess, K. Chem. Rev., 2005, 105, 3272.
53. Zhou, J.; Zhu, Y.; Burgess, K. Org. Lett., 2007, 9, 1391.
54. Perry, M. C.; Cui, X.; Powell, M. T.; Hou, D. R.; Reibenspies, J. H.; Burgess, K. J. Am. Chem. Soc., 2003, 125, 113.
55. Cui, X.; Ogle, J. W.; Burgess, K. Chem. Commun., 2005, 672.
56. Nanchen, S.; Pfaltz, A. Chem. Eur. J., 2006, 12, 4550.
57. Nanchen, S.; Pfaltz, A. Helv. Chim. Acta 2006, 89, 1559.
58. Kallstrom, K.; Andersson, P. G. Tetrahedron Lett., 2006, 47, 7477.
59. Bolm, C.; Focken, T.; Raabe, G. Tetrahedron Asymmetry, 2003, 14, 1733.
60. Chen, D.; Banphavichit, V.; Reibenspies, J.; Burgess, K. Organometallics, 2007, 26, 855.
61. Baskakov, D.; Herrmann, W. A.; Herdtweck, E.; Hoffmann, S. D. Organometallics, 2007, 26, 626.
62. Lee, S.; Hartwig, J. F. J. Org. Chem., 2001, 66, 3402.
63. Kundig, P. E.; Seidel, T. M.; Jia, Y.; Bernardine lli, G. Angew. Chem. Int. Ed., 2007, 46, 8484.
64. Glorius, F. Altenhoff, G.; Goddard, R.; Lehmann, C. Chem. Commun., 2002, 2704.
65. Arao, T.; Kondo, K.; Aoyama, T. Tetrahedron Lett., 2006, 47, 1417.
66. Bertogg, A.; Camponovo, F.; Togni, A. Eur. J. Inorg. Chem., 2005, 347.
67. Chen, T.; Xu, J.; Shi, M. Org. Lett., 2007, 9, 865.
68. Jensen, D. R.; Sigman, M. S. Org. Lett., 2003, 5, 63.
69. Ferreira, E. M., Stoltz, B. M. J. Am. Chem. Soc., 2001, 123, 7725.
70. Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc., 2001, 123, 7475.
71. Steinborn, D.; Taube, R. Z. J. Mol. Catal., 1989, 49, 235.
72. Fadini, F.; Togni, A. Chem. Commun., 2003, 30.
73. Gischig, S.; Togni, A. Eur. J. Inorg. Chem., 2005, 4745.
74. Visentin, F.; Togni, A. Organometallics, 2007, 26, 3746.
75. Bonnet, G. L.; Douthwaite, R. E.; Kariuki, B. M. Organometallics, 2003, 22, 4187.
76. Trost, B. M.; VanVranken, D. L. Chem. Rev., 1996, 96, 395.
77. Hodgson, R.; Douthwaite, R. E. J. Organomet. Chem., 2005, 690, 5822.
78. Ros, A.; Monge, D.; Alcarazo, M.; Alvarez, E.; Lassaletta, J. M.; Fernandez, R. Organometallics, 2006, 25, 6039.
79. Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne, M. R. J. Am. Chem. Soc., 2000, 122, 1905.
80. Roseblade, S. J.; Ros, A.; Monge, D.; Alcarazo, M.; Alvarez, E.; Lassaletta, J. M.; Fernandez, R. Organometallics, 2007, 26, 2570.
81. Flahaut, A.; Roland, S.; Mangeney, P. Tetrahedron Asymmetry, 2007, 18, 29.
82. Li, S.; Zhong, J.; Wang, Y. Tetrahedron Asymmetry, 2006, 17, 1650.
83. Gillingham, D. G.; Hoveyda, A. H. Angew. Chem. Int. Ed., 2007, 46, 3860.
84. Fraser, P. K.; Woodward, S. Tetrahedron Lett., 2001, 42, 2747.
85. Pytkowicz, J.; Roland, S.; Mangeney, P. Tetrahedron Asymmetry, 2001, 12, 2087.
86. Guillen, F.; Winn, C. L.; Alexakis, A. Tetrahedron Asymmetry, 2001, 12, 2083.
87. Winn, C. L.; Guillen, F., Pytkowicz, J.; Roland, S.; Mangeney, P.; Alexakis, A. J. Organomet. Chem., 2005, 690, 5672.
88. Arnold, P. L.; Rodden, M.; Davis, K. M.; Scarisbrick, A. C.; Blake, A. J.; Wilson, C. Chem. Commun., 2004, 1612.
89. Clavier, H.; Coutable, L.; Guillemin, J. C.; Mauduit, M. Tetrahedron Asymmetry, 2005, 16, 921.
90. Clavier, H.; Coutable, L.; Toupet, L.; Guillemin, J. C.; Mauduit, M. J. Organomet. Chem., 2005, 690, 5237.
91. Cavell, K. J.; Elliot, M. C.; Nielson, D. J.; Paine, J. S. Dalton Trans., 2006, 4922.
92. Martin, D.; Kehrli, S.; d'Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. J. Am. Chem. Soc., 2006, 128, 8416.
93. Lee, K.; Brown, K. M.; Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc., 2006, 128, 7182.
94. Brown, K. M.; May, T. L.; Baxter, C. A.; Hoveyda, A. H. Angew. Chem. Int. Ed., 2007, 46, 1097.
95. Clavier, H.; Guillemin, J. C.; Mauduit, M. Chirality, 2007, 19, 471.
96. Jurcik, V.; Gilani, M.; Wilhelm, R. Eur. J. Org. Chem., 2006, 5103.
97. Tominaga, S.; Oi, Y.; Kato, T.; An, D. K.; Okamoto, S. Tetrahedron Lett., 2004, 45, 5585.
98. Larsen, A. O.; Len, W.; Oberhuber, C. N.; Campbell, J. E.; Hoveyda, A. H. J. Am. Chem. Soc., 2004, 126, 11130.
99. Chaulagain, M. R.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc., 2007, 129, 9568.
100. Ng, S-S.; Jamison, T. F. Tetrahedron, 2006, 62, 11350.
101. Wanniarachchi, Y.A.; Slaughter, L.M. Chem. Commun., 2007, 3294.
102. Scarborough, C.C.; Grady, M.J.W.; Guzei, I.A.; Gandhi, B.A.;
103. Bunel, E.E.; Stahl, S.S. Angew. Chem. Int. Ed., 2005, 44, 5269.
104. Scarborough, C.C.; Popp, B.V.; Guzei, I.A.; Stahl, S.S. J. Organomet. Chem., 2005, 690, 6143.