Preparation of chiral phosphinoferrocene carboxamide ligands and their application to palladium-catalyzed asymmetric allylic alkylation

Organometallics

Volumn 26, Issue 20, 2007, Pages 5042-5049

  Lamač, Martin ^a   Tauchman, Jiří ^a   Císařová, Ivana ^a   Štěpnička, Petr ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; REACTION KINETICS;

CHIRAL DISCRIMINATION; DIMETHYL MALONATE; PHOSPHINOFERROCENE CARBOXAMIDES;

AROMATIC COMPOUNDS;

EID: 34948839034     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700542s     Document Type: Article

References (85)

1. (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395422.
2. (b) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
3. (c) Trost, B. M. J. Org. Chem. 2004, 69, 5813-5837.
4. (d) Hayashi, T. Asymmetric Allylic Substitution and Grignard Cross-Coupling. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 7.1, pp 325-365.
5. (e) Graening, T.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2003, 42, 2580-2584.
6. (f) Helmchen, G. J. Organomet. Chem. 1999, 576, 203214.
7. (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276.
8. Reviews: (a) Hayashi, T. Asymmetric Catalysis with Chiral Ferrocenylphosphine Ligands. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995; Chapter 2, pp 105-142.
9. (b) Togni, A. New Chiral Ferrocenyl Ligands for Asymmetric Catalysis. In Metallocenes; Togni, A., Halterman, R. L., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2, Chapter 11, pp 685-721.
10. (c) Arrayáss, R. G.; Adrio, A.; Carretero, J. G Angew. Chem., Int. Ed. 2006, 45, 7674-7715.
11. (d) Barbaro, P.; Bianchini, C.; Giambastiani, G.; Parisel, S. L. Coord. Chem. Rev. 2004, 248, 2131-2150.
12. (e) Colacot, T. J. Chem. Rev. 2003, 103, 3101-3118.
13. (f) Blaser, H.-U.; Brieden, W.; Pugin, B.; Spindler, F.; Studer, M.; Togni, A. Top. Catal. 2002, 19, 3-16.
14. (g) Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407.
15. (a) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327-9343.
16. (b) Trost, B. M.; Breit, B.; Peukert, S.; Zambrano, J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2386-2388.
17. (c) Lloyd-Jones, G. C.; Stephen, S. C.; Fairlamb, I. J. S.; Martorell, A.; Dominguez, B.; Tomlin, P. M.; Murray, M.; Fernandez, J, M.; Jeffery, J. G; Riis-Johannessen, T.; Guerziz, T. Pure Appl. Chem. 2004, 76, 589-601, and references therein.
18. (a) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064.
19. (b) Kim, Y. K.; Lee, S. J.; Ahn, K. H. J. Org. Chem. 2000, 65, 7807-7813.
20. Representative examples: (a) Gilbertson, S. R.; Lan, P. Org. Un. 2001, 3, 2237-2240.
21. (b) Dai, W.-M.; Yeung, K. K. Y.; Liu, J.-T.; Zhang, Y.; Williams, I. D. Org. Lett. 2002, 4, 1615-1619, and references therein.
22. (c) Lee, Y.-H.; Kim, Y. K.; Son, J.-H.; Ahn, K. H. Bull. Korean Chem. Soc. 2003, 23, 225-228.
23. (a) Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202.
24. (b) Hayashi, T. Acc Chem. Res. 2000, 33, 354-362.
25. Gladiali, S.; Taras, R.; Ceder, R. M.; Rocamora, M.; Muller, G.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 2004, 15, 1477-1485.
26. (a) Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995-7998.
27. (b) Zhang, W.; Shimanuki, T.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem. 1999, 64, 6247-6251.
28. (a) Longmire, J. M.; Wang, B.; Zhang, X. Tetrahedron Lett. 2000, 41, 5435-5439.
29. (b) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Cao, B.-X.; Sun, J. Chem. Commun. 2000, 1933-1934.
30. You, S.-L.; Luo, Y.-M.; Deng, W.P.; Hou, X.-L.; Dai, L.-X. J. Organomet. Chem. 2001, 637-639, 845-849.
31. (c) You, S.-L.; Hou, X.-L.; Dai, L.-X. J. Organomet. Chem. 2001, 637-639, 762-766.
32. Mateus, N.; Rataboul, L.; Daran, J.-C.; Manoury, E. J. Organomet. Chem. 2006, 691, 2297-2310.
33. Boaz, N. W.; Ponasik, J. A., Jr.; Large, S. E.; Debenham, S. D. Tetrahedron: Asymmetry 2004, 15, 2451-2154.
34. Štěpnička, P. Eur. J. Inorg. Chem. 2005, 3787-3808.
35. Lamač, M.; Císařová, I.; Ště pnička, P. Eur. J. Inorg. Chem. 2007, 2274-2287.
36. Drahoňovský, D.; Císařová, I.; Štěpnička, P.; Dvořáková, H.; Maloň P.; Dvořák, D. Collect. Czech. Chem. Commun. -2001, 66, 588-604.
37. Meca, L.; Dvořák, D.; Ludvík, J.; Císařová, I.; Štěpnička, P. Organometallics 2004, 23, 2541-2551.
38. (a) Štěpnička, P.; Lamač, M.; Císařová, I. Polyhedron 2004, 23, 921-928.
39. (b) Štěpnička, P.; Schulz, J.; Císař ová, I.; Fejfarová, K. Collect. Czech. Chem. Commun. 2007, 72, 453-467.
40. (c) Kühnert, J.; Dušek, M.; Demel, J.; Lang, H.; Štìpnièka, P. Dalton Trans. 2007, 2802-2811.
41. Kraatz, H.-B. J. Inorg. Organomet. Polym. Mater. 2005, 15, 83-106.
42. (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145.
43. (b) El Gihani, M. T.; Heaney, H. Synthesis 1998, 357-375.
44. Sutcliffe, O. B.; Bryce, M. R. Tetrahedron: Asymmetry 2003, 14, 2297-2325 (review).
45. (a) Trost, B. M.; Bunt, R. G J. Am. Chem. Soc. 1998, 120, 70-79.
46. (b) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090.
47. Raghunath, M.; Gao, W.; Zhang, X. Tetrahedron: Asymmetry 2005, 16, 3676-3681.
48. You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1998, 2765-2766.
49. 3-allyl)palladium complexes with bidentate ferrocene ligands: (a) Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1995, 14, 842-847.
50. (b) Barbaro, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160-5170.
51. (c) Burckhardt, U.; Gramlich, V.; Hofmann, P.; Nesper, R.; Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1996, 15, 3496-3503.
52. (d) Fernández-Galán, R.; Jalón, F. A.; Manzano, B. R.; Rodíguez-de la Fuente, J.; Vrahami, M.; Jedlicka, B.; Weissensteiner, W.; Jogi, G. Organometallics 1997, 16, 3758-3768.
53. (e) Gómez-de la Torre, F.; Jalón, F. A.; LópezAgenjo, A.; Manzano, B. R.; Rodríguez, A.; Sturm, T.; Weissensteiner, W.; Martínez-Ripoll, M. Organometallics 1998, 17, 4634-4644.
54. (f) Tu, T.; Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X.; Dong, X.-G; Yu, Y.-H.; Sun, J. Organometallics 2003, 22, 1255-1265.
55. (g) Cho, C.-W.; Son, J.-H.; Ahn, K. H. Tetrahedron: Asymmetry 2006, 17, 2240-2246.
56. Conformers are denoted exo (endo) when the meso-CH group of the allyl moiety is directed away from (toward) the ferrocene unit.
57. 2R: (a) R = Ph: Hursthouse, M. B.; Coles, S. J.;
58. Tucker, J. H. R. Private communication to CCDC (refcode BATLEO).
59. 2OH: Štěpnička, P.; Císařová, I. CrystEngComm 2005, 7, 37-43.
60. (c) R = C≡CH: Brosch, O.; Weyhermueller, T.; Metzler-Nolte, N. Eur. J. Inorg. Chem. 2000, 323-330.
61. (d) R = Et: Oberhoff, M.; Duda, L.; Karl, J.; Mohr, R.; Erker, G.; Froehlich, R.; Grehl, M. Organometallics 1996, 15, 4005-4011.
62. 3, Z = 4 at 150 K.
63. (a) Appleton, T. G.; Clark, H. C.; Manzer-L. E. Coord. Chem. Rev. 1973, 10, 335-422.
64. (b) Hartley, F. R. The Chemistry of Platinum and Palladium; Applied Science: London, 1973; pp 299-303.
65. Selected data: Pd-O 2.101(6) Å, Pd-P 2.321(2), Pd-C(allyl transP) 2.253(7), Pd-C(allyl meso) 2.139(8), and Pd-C(allyl trans-O) 2.113(9) Åat 293 K.
66. Selected data: Pd-O 2.13(1) Å, Pd-P 2.286(6), Pd-C(allyl transP) 2.20(3), Pd-C(allyl meso) 2.10(2), and Pd-C(allyl trans-O) 2.07(2) Å at 213 K.
67. Cambridge Structural Database, version 5.28 (November 2006) with updates of January and May 2007.
68. Bosnich et al. have shown that the major allylic intermediate gives rise to the major product enantiomer: Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046-2054.
69. Theoretical calculations: (a) Bloechl. P.; Togni, A. Organometallics 1996, 15, 4125-4132.
70. (b) Ward, T. R. Organometallics 1996, 15, 2836-2838.
71. You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J. Org. Chem. 2002, 67, 4684-4695.
72. It is worth noting that I-based catalysts produce preferably (R)-6 under similar conditions.
73. Podlaha, J.; Štěpnič̀ka, P.; Císařová, I.; Ludvík, J. Organometallics 1996, 15, 543-550.
74. Štěpnička, P. New J. Chem. 2002, 26, 567-575.
75. Acetate 5 was prepared by acetylation of 1,3-diphenylallyl alcohol, which results from reduction of chalcone: (a) Kohler, E. P.; Chadwell, H. M. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. I, pp 78-80.
76. (b) Leung, W.; Cosway, S.; Jonmes, R. H. V.; McCann, H.; Wills, M. J. Chem. Soc, Perkin Trans. 1 2001, 2588-2594.
77. (c) Watson, I. D. G.; Styler, S. A.; Yudin, A. K. J. Am. Chem. Soc. 2004, 126, 5086-5087.
78. Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301-6311.
79. (a) Zang, W.; Yoneda, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1998, 9, 3371-3380.
80. Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191-194.
81. Otwinowski, Z.; Minor, W. HKL Denzo and Scalepack Program Package; Nonius BV: Delft, The Netherlands. For a reference,
82. see: Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
83. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119.
84. Sheldrick, G. M. SHELXL97, Program for Crystal Structure Refinement from Diffraction Data; University of Goettingen: Germany, 1997.
85. Spek, A. L. Platon, a multipurpose crystallographic tool; Utrecht University: Utrecht, The Netherlands, 2003, and updates. Available via the Internet at http://www.cryst.chem.uu.nl/platon/.