Sterically demanding planar chiral P,N ligands by diastereoselective ortho lithiation of pentaphenylferrocenyloxazolines and their application to palladium-catalyzed substitutions with cyclic allylic acetates

Organometallics

Volumn 33, Issue 4, 2014, Pages 1068-1078

  Ayerbe Garcia, Marta ^a   Frey, Wolfgang ^a   Peters, René ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84894676276     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500049f     Document Type: Article

References (74)

1. Chiral Ferrocenes in Asymmetric Catalysis. Synthesis and Applications; Dai, L.-X., Hou, X.-L.; Eds.; Wiley-VCH: Weinheim, Germany, 2009.
2. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377
3. Ferrocenes; Hayashi, T.; Togni, A.; Eds.; VCH: Weinheim, Germany, 1995.
4. Drusan, M.; Šebesta, R. Tetrahedron 2014, 70, 759
5. Ferrocene: Ligands, Materials and Biomolecules; Štepnička, P.; Ed.; Wiley: Chichester, U.K., 2008.
6. Peters, R.; Fischer, D.; Jautze, S. Top. Organomet. Chem. 2011, 33, 139-175.
7. Asymmetric Catalysis on Industrial Scale; Blaser, H. U.; Schmidt, E.; Eds.; Wiley-VCH: Weinheim, Germany, 2004.
8. Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389
9. Ganter, C.; Wagner, T. Chem. Ber. 1995, 128, 1157
10. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74
11. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10
12. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79
13. Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511
14. Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733
15. Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, 1462
16. Enders, D.; Peters, R.; Lochtman, R.; Raabe, G. Angew. Chem., Int. Ed. 1999, 38, 2421
17. Enders, D.; Peters, R.; Lochtman, R.; Raabe, G.; Runsink, J.; Bats, J. W. Eur. J. Org. Chem. 2000, 3399
18. Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Eur. J. Org. Chem. 2000, 2839
19. Peters, R.; Fischer, D. F. Org. Lett. 2005, 7, 4137
20. Vinci, D.; Mateus, N.; Wu, X.; Hancock, F.; Steiner, A.; Xiao, J. Org. Lett. 2006, 8, 215
21. Tsukazaki, M.; Tinkl, M.; Roglans, A.; Taylor, N. J.; Snieckus J. Am. Chem. Soc. 1996, 118, 685
22. Ortho lithiation of amines: Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Togni, A.; Albinati, A.; Müller, B. Organometallics 1994, 13, 4481
23. Ortho lithiation of an acetal: Wölfle, H.; Kopacka, H.; Wurst, K.; Ongania, K.-H.; Görtz, H.-H.; Preishuber-Pflügl, P.; Bildstein, B. J. Organomet. Chem. 2006, 691, 1197
24. Ortho lithiation of oxazolines: Geisler, F. M.; Helmchen, G. J. Org. Chem. 2006, 71, 2486
25. Ortho lithiation of imidazolines: Peters, R.; Xin, Z.-q.; Fischer, D. F.; Schweizer, W. B. Organometallics 2006, 25, 2917
26. Ortho palladation of imidazolines: Weiss, M. E.; Fischer, D. F.; Xin, Z.-q.; Jautze, S.; Schweizer, W. B.; Peters, R. Angew. Chem., Int. Ed. 2006, 45, 5694
27. Fischer, D. F.; Barakat, A.; Xin, Z.-q.; Weiss, M. E.; Peters, R. Chem. Eur. J. 2009, 15, 8722
28. Butler, D. C. D.; Richards, C. J. Organometallics 2002, 21, 5433
29. Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091
30. Bellemin-Laponnaz, S.; Twedel, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009
31. Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794
32. Mermerian, A. H.; Fu, G. C. Angew. Chem., Int. Ed. 2005, 44, 949
33. Mermerian, A. H.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 5604
34. Mermerian, A. H.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 4050
35. Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921
36. Eitel, S. H.; Jautze, S.; Frey, W.; Peters, R. Chem. Sci. 2013, 4, 2218
37. Weber, M.; Peters, R. J. Org. Chem. 2012, 77, 10846
38. 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
39. Peters, R.; Xin, Z.-q.; Maier, F. Chem. Asian J. 2010, 5, 1770
40. Xin, Z.-q.; Fischer, D. F.; Peters, R. Synlett 2008, 1495
41. Fischer, D. F.; Xin, Z.-q.; Peters, R. Angew. Chem., Int. Ed. 2007, 46, 7704
42. Tsuji, J. Palladium Reagents and Catalysis, Innovations in Organic Synthesis; Wiley: New York, 1995.
43. Trost, B. M.; van Vranken, D. L. Chem. Rev. 1996, 96, 395
44. Helmchen, G. J. Organomet. Chem. 1999, 576, 203
45. Helmchen, G.; Steinhagen, H.; Kudis, S. In Transition Metal Catalysed Reactions-Chemistry for the 21st Century Monographs; Murahashi, S.; Davies, S. G., Eds.; Blackwell: Oxford, U.K., 1999; pp 241-260.
46. Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Heidelberg, Germany, 1999; pp 833-886.
47. Trost, B. M.; Lee, C. A. Catalytic Asymmetric Synthesis, 2 nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 593-649.
48. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336
49. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921
50. Masdeu-Bultó, A. M.; Diéguez, M.; Martín, E.; Gómez, M. Coord. Chem. Rev. 2003, 242, 159
51. Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258
52. Helmchen, G.; Kazmaier, U.; Foerster, S. In Catalytic Asymmetric Synthesis, 3 rd ed.; Ojima, I.; Ed.; Wiley, Hoboken, NJ, 2010; pp 497-641.
53. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047
54. Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845
55. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089
56. Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750
57. Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994
58. Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905
59. Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919
60. Jones, G.; Richards, C. J. Tetrahedron: Asymmetry 2004, 15, 653
61. Pamies, O.; Dieguez, M.; Claver, C. J. Am. Chem. Soc. 2005, 127, 3646
62. See ref 11c.
63. Schlögl, K. Top. Stereochem. 1967, 1, 39
64. Herbert, S. A.; Castell, D. C.; Clayden, J.; Arnott, G. E. Org. Lett. 2013, 15, 3334
65. Supplemantary crystallographic data for this paper have been deposited with the Cambridge Crystallographic Data Centre as depositions CCDC 957957 (9a), CCDC 957958 (9b), and CCDC 957959 (13). 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/.
66. Kollmar, M.; Goldfuss, B.; Reggelin, M.; Rominger, F.; Helmchen, G. Chem. Eur. J. 2001, 7, 4913
67. Kollmar, M.; Steinhagen, H.; Janssen, J. P.; Goldfuss, B.; Malinovskaya, S. A.; Vázquez, J.; Rominger, F.; Helmchen, G. Chem. Eur. J. 2002, 8, 3103
68. Zehnder, M.; Schaffner, S.; Neuburger, M.; Plattner, D. A. Inorg. Chim. Acta 2002, 337, 287
69. Hartley, F. R. Chem. Soc. Rev. 1973, 2, 163
70. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5 th ed.; Wiley-Interscience: New York, 1999; pp 1299-1300.
71. Khobragade, D. A.; Mahamulkar, S. G.; Pospíšil, L.; Císařová, I.; Rulíšek, L.; Jahn, U. Chem. Eur. J. 2012, 18, 12267
72. Trost, B. M.; Strege, P. E; Weber, L.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3407
73. Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905
74. Cheung, H. Y.; Yu, W. Y.; Terry, T. L; Yeung, A.; Zhou, Z.; Chan, A. S. C. Adv. Synth. Catal. 2009, 351, 1412