Helicene-based phosphite ligands in asymmetric transition-metal catalysis: Exploring Rh-catalyzed hydroformylation and Ir-catalyzed allylic amination

European Journal of Organic Chemistry

Volumn , Issue 20-21, 2011, Pages 3849-3857

  Krausová, Zuzana ^a   Sehnal, Petr ^a   Bondzic, Bojan P ^b   Chercheja, Serghei ^b   Eilbracht, Peter ^b   Stará, Irena G ^a   Šaman, David ^a   Starý, Ivo ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Amination; Asymmetric catalysis; Helical structures; Hydroformylation; P ligands

Indexed keywords

EID: 79960319418     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100259     Document Type: Article

References (96)

1. E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999 along with Supplements 1 and 2 (2004).
2. Q.-L. Zhou (Ed.), Privileged Chiral Ligands and Catalysts, Wiley, Hoboken, 2011.
3. For "privileged chiral catalysts", see, T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691-1693.
4. I. C. Lennon, C. J. Pilkington, Synthesis 2003, 1639-1642.
5. M. J. Burk, Acc. Chem. Res. 2000, 33, 363-372.
6. M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518-8519.
7. R. Noyori, Angew. Chem. Int. Ed. 2002, 41, 2008-2022.
8. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, K. Toriumi, T. Ito, J. Am. Chem. Soc. 1980, 102, 7932-7934.
9. H.-U. Blaser, B. Pugin, F. Spindler, M. Thommen, Acc. Chem. Res. 2007, 40, 1240-1250.
10. R. G. Arrayás, J. Adrio, J. C. Carretero, Angew. Chem. Int. Ed. 2006, 45, 7674-7715.
11. H. U. Blaser, W. Brieden, B. Pugin, F. Spindler, M. Studer, A. Togni, Top. Catal. 2002, 19, 3-16.
12. A. Togni, Chimia 1996, 50, 86-93.
13. E. M. McGarrigle, D. G. Gilheany, Chem. Rev. 2005, 105, 1563-1602.
14. W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. 1990, 112, 2801-2803.
15. J. F. Teichert, B. L. Feringa, Angew. Chem. Int. Ed. 2010, 49, 2486-2528.
16. K. Mikami, M. Lautens (Eds.), New Frontiers in Asymmetric Catalysis, Wiley, Hoboken, 2007.
17. A. Börner (Ed.), Phosphorus Ligands in Asymmetric Catalysis, Wiley-VCH, Weinheim, 2008.
18. For selected reviews, see I. G. Stará, I. Starý in Science of Synthesis (Eds:, J. S. Siegel, Y. Tobe), Thieme, Stuttgart, 2010, vol. 45b, pp. 885-953.
19. I. Starý, I. G. Stará in Strained Hydrocarbons (Ed.:, H. Dodziuk), Wiley-VCH, Weinheim, 2009, pp. 166-176.
20. A. Rajca, M. Miyasaka in Functional Organic Materials (Eds.:, T. J. J. Müller, U. H. F. Bunz), Wiley-VCH, Weinheim, 2007, pp. 547-581.
21. A. Urbano, Angew. Chem. Int. Ed. 2003, 42, 3986-3989.
22. H. Hopf in Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives, Wiley-VCH, Weinheim, 2000, pp. 323-330.
23. T. J. Katz, Angew. Chem. Int. Ed. 2000, 39, 1921-1923.
24. G. Oremek, U. Seiffert, A. Janecka, Chem.-Ztg. 1987, 111, 69-75.
25. F. Vögtle, Fascinating Molecules in Organic Chemistry, Wiley, New York, 1992, pp. 156-180.
26. K. P. Meurer, F. Vögtle, Top. Curr. Chem. 1985, 127, 1-76.
27. W. H. Laarhoven, W. J. C. Prinsen, Top. Curr. Chem. 1984, 125, 63-130.
28. Helicenes were also used in stoichiometric asymmetric reactions as chiral auxiliaries (in diastereoselective reduction of α-keto esters, ene reaction, and atrolactic synthesis) or chiral reagents (in hydroxyamination and epoxidation of olefins). For more details, see B. Ben Hassine, M. Gorsane, J. Pecher, R. H. Martin, Bull. Soc. Chim. Belg. 1987, 96, 801-808.
29. B. Ben Hassine, M. Gorsane, F. Geerts-Evrard, J. Pecher, R. H. Martin, D. Castelet, Bull. Soc. Chim. Belg. 1986, 95, 557-566.
30. B. Ben Hassine, M. Gorsane, J. Pecher, R. H. Martin, Bull. Soc. Chim. Belg. 1986, 95, 547-556.
31. B. Ben Hassine, M. Gorsane, J. Pecher, R. H. Martin, Bull. Soc. Chim. Belg. 1985, 94, 759-769.
32. B. Ben Hassine, M. Gorsane, J. Pecher, R. H. Martin, Bull. Soc. Chim. Belg. 1985, 94, 597-603.
33. A. Terfort, H. Görls, H. Brunner, Synthesis 1997, 79-86.
34. M. T. Reetz, E. W. Beuttenmüller, R. Goddard, Tetrahedron Lett. 1997, 38, 3211-3214.
35. M. T. Reetz, S. Sostmann, J. Organomet. Chem. 2000, 603, 105-109.
36. I. Sato, R. Yamashima, K. Kadowaki, J. Yamamoto, T. Shibata, K. Soai, Angew. Chem. Int. Ed. 2001, 40, 1096-1098.
37. T. Kawasaki, K. Suzuki, E. Licandro, A. Bossi, S. Maiorana, K. Soai, Tetrahedron: Asymmetry 2006, 17, 2050-2053.
38. S. D. Dreher, T. J. Katz, K.-C. Lam, A. L. Rheingold, J. Org. Chem. 2000, 65, 815-822.
39. D. Nakano, M. Yamaguchi, Tetrahedron Lett. 2003, 44, 4969-4971.
40. J. Chen, N. Takenaka, Chem. Eur. J. 2009, 15, 7268-7276.
41. N. Takenaka, R. S. Sarangthem, B. Captain, Angew. Chem. Int. Ed. 2008, 47, 9708-9710.
42. J. Chen, B. Captain, N. Takenaka, Org. Lett. 2011, 13, 1654-1657.
43. N. Takenaka, J. Chen, B. Captain, R. S. Sarangthem, A. Chandrakumar, J. Am. Chem. Soc. 2010, 132, 4536-4537.
44. M. Šámal, J. Míšek, I. G. Stará, I. Starý, Collect. Czech. Chem. Commun. 2009, 74, 1151-1159.
45. M. R. Crittall, H. S. Rzepa, D. R. Carbery, Org. Lett. 2011, 13, 1250-1253.
46. M. T. Reetz, G. Mehler, Angew. Chem. Int. Ed. 2000, 39, 3889-3890.
47. C. Claver, E. Fernandez, A. Gillon, K. Heslop, D. J. Hyett, A. Martorell, A. G. Orpen, P. G. Pringle, Chem. Commun. 2000, 961-962.
48. M. van den Berg, A. J. Minnaard, E. P. Schudde, J. van Esch, A. H. M. de Vries, J. G. de Vries, B. L. Feringa, J. Am. Chem. Soc. 2000, 122, 11539-11540.
49. Helicenes are defined as polycyclic aromatic compounds consisting of all-ortho-fused benzene or heteroarene (e.g., thiophene) rings. However, modification of the helicene skeleton can go further, displacing one or more five/six-membered arenes by five/six/seven-membered, partially saturated carbocycles or heterocycles. Such molecules can be referred to as helicene-like structures, as they usually keep the molecular shape of the parent helicenes. For representative examples, see A. Andronova, F. Szydlo, F. Teplý, M. Tobrmanová, A. Volot, I. G. Stará, I. Starý, L. Rulíšek, D. Šaman, J. Cvačka, P. Fiedler, P. Vojtíšek, Collect. Czech. Chem. Commun. 2009, 74, 189-215.
50. P. Sehnal, Z. Krausová, F. Teplý, I. G. Stará, I. Starý, L. Rulíšek, D. Šaman, I. Císař ová, J. Org. Chem. 2008, 73, 2074-2082.
51. I. Starý, I. G. Stará, Z. Alexandrová, P. Sehnal, F. Teplý, D. Šaman, L. Rulíšek, Pure Appl. Chem. 2006, 78, 495-499.
52. I. G. Stará, Z. Alexandrová, F. Teplý, P. Sehnal, I. Starý, D. Šaman, M. Buděšínský, J. Cvačka, Org. Lett. 2005, 7, 2547-2550.
53. I. G. Stará, Z. Alexandrová, F. Teplý, P. Sehnal, I. Starý, D. Šaman, M. Buděšínský, J. Cvačka, Collect. Czech. Chem. Commun. 2003, 68, 917-930.
54. I. G. Stará, I. Starý, A. Kollárovič, F. Teplý, Š. Vyskočil, D. Šaman, Tetrahedron Lett. 1999, 40, 1993-1996.
55. I. G. Stará, I. Starý, A. Kollárovič, F. Teplý, D. Šaman, M. Tichý, J. Org. Chem. 1998, 63, 4046-4050.
56. F. Teplý, I. G. Stará, I. Starý, A. Kollárovič, D. Šaman, Š. Vyskočil, P. Fiedler, J. Org. Chem. 2003, 68, 5193-5197.
57. J. Míšek, F. Teplý, I. G. Stará, M. Tichý, D. Šaman, I. Císařová, P. Vojtíšek, I. Starý, Angew. Chem. Int. Ed. 2008, 47, 3188-3191.
58. C. Vallée, Y. Chauvin, J.-M. Basset, C. C. Santini, J.-C. Galland, Adv. Synth. Catal. 2005, 347, 1835-1847.
59. I. M. Malkowsky, M. Nieger, O. Kataeva, S. R. Waldvogel, Synthesis 2007, 773-778.
60. N. L. H. L. Broeders, L. H. Koole, H. M. Buck, J. Am. Chem. Soc. 1990, 112, 7475-7482.
61. A. Granata, D. S. Argyropoulos, J. Agric. Food Chem. 1995, 43, 1538-1544.
62. A. Zwierzak, Can. J. Chem. 1967, 45, 2501-2512.
63. P. W. N. M. Van Leeuwen, C. Claver, Rhodium-Catalysed Hydroformylation, Kluwer Academic, Dordrecht, 2000.
64. For reviews, see A. Gual, C. Godard, S. Castillõn, C. Claver, Tetrahedron: Asymmetry 2010, 21, 1135-1146.
65. J. Klosin, C. R. Landis, Acc. Chem. Res. 2007, 40, 1251-1259 and references cited therein
66. B. Breit, W. Seiche, Synthesis 2001, 1-36.
67. For recent examples, see A. L. Watkins, C. R. Landis, Org. Lett. 2011, 13, 164-167.
68. X. Zhang, B. Cao, S. Yu, X. Zhang, Angew. Chem. Int. Ed. 2010, 49, 4047-4050.
69. X. Zhang, B. Cao, Y. Yan, S. Yu, B. Ji, X. Zhang, Chem. Eur. J. 2010, 16, 871-877.
70. G. M. Noonan, C. J. Cobley, T. Lebl, M. L. Clarke, Chem. Eur. J. 2010, 16, 12788-12791.
71. G. M. Noonan, D. Newton, C. J. Cobley, A. Suárez, A. Pizzano, M. L. Clarke, Adv. Synth. Catal. 2010, 352, 1047-1054.
72. S. Chercheja, S. K. Nadakudity, P. Eilbracht, Adv. Synth. Catal. 2010, 352, 637-643.
73. A. Gual, C. Godard, S. Castillõn, C. Claver, Adv. Synth. Catal. 2010, 352, 463-477.
74. J. Mazuela, O. Pàmies, M. Diéguez, L. Palais, S. Rosset, A. Alexakis, Tetrahedron: Asymmetry 2010, 21, 2153-2157.
75. A. D. Worthy, C. L. Joe, T. E. Lightburn, K. L. Tan, J. Am. Chem. Soc. 2010, 132, 14757-14759.
76. R. I. McDonald, G. W. Wong, R. P. Neupane, S. S. Stahl, C. R. Landis, J. Am. Chem. Soc. 2010, 132, 14027-14029.
77. A. L. Watkins, C. R. Landis, J. Am. Chem. Soc. 2010, 132, 10306-10317.
78. For (+)-(S)- 30a, see:, T. Hayashi, M. Konishi, M. Fukushima, T. Mise, M. Kagotani, M. Tajika, M. Kumada, J. Am. Chem. Soc. 1982, 104, 180-186.
79. for (-)-(S)- 32a, see:, N. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am. Chem. Soc. 1993, 115, 7033-7034.
80. for (+)-(S)- 35a, see:, J. S. Yadav, A. Bandyopadhyay, B. V. S. Reddy, Tetrahedron Lett. 2001, 42, 6385-6388. Optical rotation of (R)- or (S)-enantiomers of 31a and 36a-38a have not been published.
81. Y. Yan, X. Zhang, J. Am. Chem. Soc. 2006, 128, 7198-7202.
82. U. Nettekoven, P. C. J. Kamer, M. Widhalm, P. W. N. M. van Leeuwen, Organometallics 2000, 19, 4596-4607.
83. For reviews, see G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675-691.
84. G. Helmchen in Iridium Complexes in Organic Synthesis (Eds.:, L. A. Oro, C. Claver), Wiley-VCH, Weinheim, 2009, pp. 211-250.
85. R. Takeuchi, S. Kezuka, Synthesis 2006, 3349-3366.
86. H. Miyabe, Y. Takemoto, Synlett 2005, 1641-1655.
87. F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427.
88. T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 15164-15165.
89. J. A. Raskatov, S. Spiess, C. Gnamm, K. Brödner, F. Rominger, G. Helmchen, Chem. Eur. J. 2010, 16, 6601-6615.
90. D. Marković, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 11680-11681.
91. A. Leitner, S. Shekhar, M. J. Pouy, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 15506-15514.
92. C. A. Kiener, C. Shu, C. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14272-14273.
93. J. Lehmann, G. C. Lloyd-Jones, Tetrahedron 1995, 51, 8863-8874.
94. B. P. Bondzic, A. Farwick, J. Liebich, P. Eilbracht, Org. Biomol. Chem. 2008, 6, 3723-3731.
95. C. Welter, R. M. Moreno, S. Streiff, G. Helmchen, Org. Biomol. Chem. 2005, 3, 3266-3268.
96. A. M. Schmidt, P. Eilbracht, J. Org. Chem. 2005, 70, 5528-5535.