Cooperative bimetallic asymmetric catalysis: Comparison of a planar chiral ruthenocene bis-palladacycle to the corresponding ferrocene

ACS Catalysis

Volumn 4, Issue 6, 2014, Pages 1850-1858

  Hellmuth, Tina ^a   Rieckhoff, Stefan ^a   Weiss, Marcel ^a   Dorst, Konstantin ^a   Frey, Wolfgang ^a   Peters, René ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

1,4 addition; cyclopalladation; imidazoline; rearrangement; ruthenocene

Indexed keywords

CATALYSIS; CATALYSTS; PALLADIUM; PALLADIUM COMPOUNDS; STEREOSELECTIVITY;

1 ,4-ADDITION; CYCLOPALLADATION; IMIDAZOLINES; REARRANGEMENT; RUTHENOCENES;

ORGANOMETALLICS;

EID: 84902201203     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs500393x     Document Type: Article

References (90)

1. Wilcox, D. E. Chem. Rev. 1996, 96, 2435-2458
2. van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54, 12985-13011
3. Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209
4. Shibasaki, M.; Matsunaga, S. Chem. Soc. Rev. 2006, 35, 269-279
5. Shibasaki, M.; Kanai, M.; Matsunaga, S.; Kumagai, N. Acc. Chem. Res. 2009, 42, 1117-1127
6. van der Vlugt, J. I. Eur. J. Inorg. Chem. 2012, 363-375
7. Park, J.; Hong, S. Chem. Soc. Rev. 2012, 41, 6931-6943
8. Bratko, I.; Gómez, M. Dalton Trans. 2013, 42, 10664-10681
9. Jautze, S.; Seiler, P.; Peters, R. Angew. Chem., Int. Ed. 2007, 46, 1260-1264
10. Jautze, S.; Seiler, P.; Peters, R. Chem. - Eur. J. 2008, 14, 1430-1444
11. Jautze, S.; Diethelm, S.; Frey, W.; Peters, R. Organometallics 2009, 28, 2001-2004
12. Nakamura, S.; Hyodo, K.; Nakamura, Y.; Shibata, N.; Toru, T. Adv. Synth. Catal. 2008, 350, 1443-1448
13. Arai, T.; Yokoyama, N. Angew. Chem., Int. Ed. 2008, 47, 4989-4992
14. Review: Liu, H.; Du, D.-M. Adv. Synth. Catal. 2009, 351, 489-519
15. Huang, H.; Peters, R. Angew. Chem., Int. Ed. 2009, 48, 604-606
16. Liu, H.; Du, D.-M. Adv. Synth. Catal. 2010, 352, 1113-1118
17. Ohara, M.; Nakamura, S.; Shibata, N. Adv. Synth. Catal. 2011, 353, 3285-3289
18. Hyodo, K.; Nakamura, S.; Tsuji, K.; Ogawa, T.; Funahashi, Y.; Shibata, N. Adv. Synth. Catal. 2011, 353, 3385-3390
19. Jautze, S.; Peters, R. Angew. Chem., Int. Ed. 2008, 47, 9284-9288
20. Eitel, S. H.; Jautze, S.; Frey, W.; Peters, R. Chem. Sci. 2013, 4, 2218-2233
21. Weber, M.; Jautze, S.; Frey, W.; Peters, R. J. Am. Chem. Soc. 2010, 132, 12222-12225
22. Weber, M.; Frey, W.; Peters, R. Adv. Synth. Catal. 2012, 354, 1443-1449
23. Weber, M.; Jautze, S.; Frey, W.; Peters, R. Chem. - Eur. J. 2012, 18, 14792-14804
24. Weber, M.; Frey, W.; Peters, R. Chem. - Eur. J. 2013, 19, 8342-8351
25. Weber, M.; Frey, W.; Peters, R. Angew. Chem., Int. Ed. 2013, 52, 13223-13227
26. Weber, M.; Klein, J. E. M. N.; Miehlich, B.; Frey, W.; Peters, R. Organometallics 2013, 32, 5810-5817
27. Hardgrove, G. L.; Templeton, D. H. Acta Crystallogr. 1959, 12, 28-32
28. Dunitz, J. D.; Orgel, L. E.; Rich, A. Acta Crystallogr. 1956, 9, 373-375
29. Review: Richards, C. J. In Chiral Ferrocenes in Asymmetric Catalysis; Dai, L.-X.; Hou, X.-L., Eds.; Wiley-VCH: Weinheim, Germany, 2010; pp 337-368.
30. Dupont, J.; Pfeffer, M. Palladacycles; Wiley-VCH: Weinheim, Germany, 2008.
31. Djukic, J.-P.; Hijazi, A.; Flack, H. D.; Bernardinelli, G. Chem. Soc. Rev. 2008, 37, 406-425
32. Kamiyama, S.-i.; Kimura, T.; Kasahara, A.; Izumi, T.; Maemura, M. Bull. Chem. Soc. Jpn. 1979, 52, 142-145
33. Butler, I. R. Organometallics 1992, 11, 74-83
34. Kuklin, S. A.; Dolgushin, F. M.; Petrovskii, P. V.; Koridze, A. A. Russ. Chem. Bull., Int. Ed. 2006, 55, 1950-1955
35. Moderately enantioselective cyclopalladation of an amine (ee ≈ 50% as judged from optical rotation data): Mamedyarova, I. A.; Nefedova, M. N.; Sokolov, V. I. J. Organomet. Chem. 1996, 524, 181-186
36. Cyclopalladation of an imine, which probably proceeds with low enantioselectivity: Troitskaya, L. L.; Ovseenko, S. T.; Sokolov, V. I.; Gruselle, M. Russ. Chem. Bull. 1998, 47, 1382-1385
37. Moderately diastereoselective cyclopalladation (dr ≈ 2:1): Troitskaya, L. L.; Starikova, Z. A.; Demeshchik, T. V.; Ovseenko, S. T.; Vorontsov, E. V.; Sokolov, V. I. J. Organomet. Chem. 2005, 690, 3976-3982
38. Mercier, A.; Wagschal, S.; Guénée, L.; Besnard, C.; Kündig, E. P. Organometallics 2013, 32, 3932-3942
39. Braunschweig, H.; Damme, A.; Hammond, K.; Mager, J. Organometallics 2012, 31, 6317-6321
40. The stereodescriptors with regard to the planar chirality are used according to Schlögl, K. Top. Stereochem. 1967, 1, 39-91
41. Supplementary crystallographic data for this compound have been deposited with the Cambridge Crystallographic Data Centre as deposition 988586. This material is available free of charge via the Internet at http://pubs.acs.org and http://www.ccdc.cam.ac.uk/products/csd/request/.
42. The same conditions have been reported for ferrocene: Breit, B.; Breuninger, D. Synthesis 2005, 2782-2786
43. Alternative protocols towards 2: Rausch, M. D.; Fischer, E. O.; Grubert, H. J. Am. Chem. Soc. 1960, 82, 76-82
44. Liu, D.; Xie, F.; Zhao, X.; Zhang, W. Tetrahedron 2008, 64, 3561-3566
45. Supplementary crystallographic data for this compound have been deposited with the Cambridge Crystallographic Data Centre as deposition 988587. This material is available free of charge via the Internet at http://pubs.acs.org and http://www.ccdc.cam.ac.uk/products/csd/request/.
46. Anderson, C. E.; Donde, Y.; Douglas, C. J.; Overman, L. E. J. Org. Chem. 2005, 70, 648-657
47. Dunina, V. V.; Gorunova, O. N.; Livantsov, M. V.; Grishin, Y. K.; Kuz'mina, L. G.; Kataeva, N. A.; Churakov, A. V. Tetrahedron: Asymmetry 2000, 11, 3967-3984
48. Zhao, G.; Yang, Q. C-.; Mak, T. C. W. Organometallics 1999, 18, 3623-3636
49. López, C.; Bosque, R.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 1996, 7, 2527-2530
50. Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221-4226
51. Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Martelletti, A.; Spencer, J.; Steiner, I.; Togni, A. Organometallics 1996, 15, 1614-1621
52. Burckhardt, U.; Baumann, M.; Trabesinger, G.; Gramlich, V.; Togni, A. Organometallics 1997, 16, 5252-5259
53. Bolm, C.; Hermanns, N.; Kesselgruber, M.; Hildebrand, J. P. J. Organomet. Chem. 2001, 624, 157-161
54. Liu, D. L.; Xie, F.; Zhang, W. J. Org. Chem. 2007, 72, 6992-6997
55. Liu, D.; Xie, F.; Zhang, W. Tetrahedron Lett. 2007, 48, 585-588
56. Xie, F.; Liu, D.; Zhang, W. Tetrahedron Lett. 2008, 49, 1012-1015
57. Nomura, H.; Richards, C. J. Chem. - Asian J. 2010, 5, 1726-1740
58. Hollis, T. K.; Overman, L. E. J. Organomet. Chem. 1999, 576, 290-299
59. Overman, L. E.; Carpenter, N. E. Org. React. 2005, 66, 1-107
60. Peters, R.; Fischer, D. F.; Jautze, S. Top. Organomet. Chem. 2011, 33, 139-175
61. Weiss, M.; Frey, W.; Peters, R. Organometallics 2012, 31, 6365-6372
62. Overman, L. E.; Owen, C. E.; Pavan, M. M.; Richards, C. J. Org. Lett. 2003, 5, 1809-1812
63. Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413
64. Kirsch, S. F.; Overman, L. E.; Watson, M. P. J. Org. Chem. 2004, 69, 8101-8104
65. Prasad, R. S.; Anderson, C. E.; Richards, C. J.; Overman, L. E. Organometallics 2005, 24, 77-81
66. Peters, R.; Xin, Z.-q.; Fischer, D. F.; Schweizer, W. B. Organometallics 2006, 25, 2917-2920
67. Weiss, M. E.; Fischer, D. F.; Xin, Z.-q.; Jautze, S.; Schweizer, W. B.; Peters, R. Angew. Chem., Int. Ed. 2006, 45, 5694-5699
68. Fischer, D. F.; Xin, Z.-q.; Peters, R. Angew. Chem., Int. Ed. 2007, 46, 7704-7707
69. Nomura, H.; Richards, C. J. Chem. - Eur. J. 2007, 13, 10216
70. Xin, Z.-q.; Fischer, D. F.; Peters, R. Synlett 2008, 1495-1499
71. Fischer, D. F.; Barakat, A.; Xin, Z.-q.; Weiss, M. E.; Peters, R. Chem. - Eur. J. 2009, 15, 8722-8741
72. Peters, R.; Xin, Z.-q.; Maier, F. Chem. - Asian J. 2010, 5, 1770-1774
73. Jiang, G.; Halder, R.; Fang, Y.; List, B. Angew. Chem., Int. Ed. 2011, 50, 9752-9755
74. Eitel, S. H.; Bauer, M.; Schweinfurth, D.; Deibel, N.; Sarkar, B.; Kelm, H.; Krüger, H.-J.; Frey, W.; Peters, R. J. Am. Chem. Soc. 2012, 134, 4683-4693
75. Watson, M. P.; Overman, L. E.; Bergman, R. G. J. Am. Chem. Soc. 2007, 129, 5031-5044
76. Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688-1690
77. Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279-1300
78. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J.; Baro, A., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
79. Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473-1482
80. Review: Jautze, S.; Peters, R. Synthesis 2010, 365-388
81. Mosey, R. A.; Fisk, J. S.; Tepe, J. J. Tetrahedron: Asymmetry 2008, 19, 2755-2762
82. Alba, A.-N. R.; Rios, R. Chem. - Asian J. 2011, 6, 720-734
83. Weber, M.; Peters, R. J. Org. Chem. 2012, 77, 10846-10855
84. Tietze, L. F. Chem. Rev. 1996, 96, 115-136
85. Enders, D.; Grondal, C.; Huettl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570-1581
86. Clavier, H.; Pellissier, H. Adv. Synth. Catal. 2012, 354, 3347-3403
87. Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278-1293
88. Ono, N. The nitro group in organic synthesis; Wiley-VCH: New York, 2001.
89. Reviews about the Nef-reaction: Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017-1047
90. Pinnick, H. W. Org. React. 1990, 38, 655-792