Mechanistic investigations of cooperative catalysis in the enantioselective fluorination of epoxides

Journal of the American Chemical Society

Volumn 133, Issue 40, 2011, Pages 16001-16012

  Kalow, Julia A ^a   Doyle, Abigail G ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AXIAL LIGATION; CATALYST SYSTEM; CO CATALYSTS; COBALT FLUORIDE; COCATALYST; COOPERATIVE CATALYSIS; COOPERATIVITY; DIMER DISSOCIATION; ENANTIOSELECTIVE; FIRST-ORDER DEPENDENCE; IN-SITU; MECHANISTIC STUDIES; NMR ANALYSIS; NONLINEAR EFFECT; NUCLEOPHILIC FLUORINE; PET TRACER; RATE LIMITING; RING OPENING; RING OPENING OF EPOXIDE; RING OPENING REACTION; SUBSTITUENT EFFECT; TURNOVER NUMBER;

CATALYSTS; COBALT; ENANTIOSELECTIVITY; FLUORINATION; HALOGENATION; ORGANIC COMPOUNDS; REACTION KINETICS;

FLUORINE;

COBALT FLUORIDE; EPOXIDE; FLUORINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; KINETICS; POSITRON EMISSION TOMOGRAPHY; RING OPENING;

CATALYSIS; COBALT; EPOXY COMPOUNDS; ETHYLENEDIAMINES; FLUORIDES; HALOGENATION; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 80053478660     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja207256s     Document Type: Article

References (94)

1. Banks, R. E., Smart, B. E., and Tatlow, J. C., Eds. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994. For recent reviews of the role of fluorine in medicinal chemistry, see
2. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
3. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359-4369
4. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
5. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319
6. Furuya, T.; Kuttruff, C. A.; Ritter, T. Curr. Opin. Drug Discovery Dev. 2008, 11, 803-819 and references therein
7. For a review, see: Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008, 108, 1501-1516
8. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1-PR43
9. Lectard, S.; Hamashima, Y.; Sodeoka, M. Adv. Synth. Catal. 2010, 352, 2708-2732
10. Clark, J. H. Chem. Rev. 1980, 80, 429-452
11. Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 3268-3269
12. Katcher, M. H.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 17402-17404
13. Bruns, S.; Haufe, G. J. Fluorine Chem. 2000, 104, 247-254
14. Haufe, G.; Bruns, S. Adv. Synth. Catal. 2002, 344, 165-171
15. Olah, G. A.; Welch, J. T.; Vankar, Y. D.; Nojima, M.; Kerekes, I.; Olah, J. A. J. Org. Chem. 1979, 44, 3872-3881
16. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431
17. Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924-10925
18. Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 10780-10781
19. Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360-1362
20. Zhu, X.; Venkatasubbaiah, K.; Weck, M.; Jones, C. W. ChemCatChem 2010, 2, 1252-1259
21. Haak, R. M.; Wezenberg, S. J.; Kleij, A. W. Chem. Commun. 2010, 46, 2713-2723
22. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302-4320
23. Oxidation occurs readily in the presence of air and acid: Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776
24. 2 and stored over activated 3 Å molecular sieves: Shaw, T. W.; Kalow, J. A.; Doyle, A. G. Org. Synth. 2012, 89, 9-18
25. Alternatively, unproductive H-bonding interactions between HFIP and various Lewis basic components of the reaction could account for this rate inhibition. HFIP is well known to have unique properties as a solvent and additive: Shuklov, I. A.; Dobrovina, N. V.; Börner, A. Synthesis 2007, 2925-2943
26. Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96-136
27. All of the substrates employed react selectively under these conditions, confirming that unselective background reaction is not responsible for the differences in rate. Selectivity factor s is calculated here from the conversion (C) and ee (ee) of epoxide: s = ln[(1 - C)(1 - ee)]/ln[(1 - C)(1 + ee)]. For a discussion of kinetic resolutions, see: Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5-26
28. m were obtained from: Speight, J. G. In Lange's Handbook of Chemistry, 16 th ed.; McGraw-Hill: New York, 2005; Chapter 2.19, pp 2.702-2.709. For Hammett correlations of the rate data using other σ constants, see the Supporting Information.
29. Wheeler, S. E.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10854-10855
30. Wheeler, S. E.; McNeil, A. J.; Müller, P.; Swager, T. M.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 3304-3311
31. Pedragosa-Moreau, S.; Morisseau, C.; Zylber, J.; Archelas, A.; Baratti, J.; Furstoss, R. J. Org. Chem. 1996, 61, 7402-7407
32. Laird, R. M.; Parker, R. E. J. Am. Chem. Soc. 1961, 83, 4277-4281
33. Blumenstein, J. J.; Ukachukwu, V. C.; Mohan, R. S.; Whalen, D. L. J. Org. Chem. 1993, 58, 924-932
34. cat is not meaningful. See: Johnson, D. W.; Singleton, D. A J. Am. Chem. Soc. 1999, 121, 9307-9312
35. Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 545-553
36. Blackmond, D. G. Acc. Chem. Res. 2000, 33, 402-411
37. Kina, A.; Iwamura, H.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 3904-3905
38. Duan, W.-L.; Iwamura, H.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 2130-2138
39. Yamagiwa, N.; Qin, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13419-13427
40. Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922-2959
41. K is a property of the catalyst and should be independent of the substrate (for an exception, see Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800-9809), but g is dependent on substrate
42. For an example in the Sharpless asymmetric epoxidation, see: Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357
43. Nielsen, L. P. C. Ph.D. Thesis, Harvard University, 2006.
44. Wu, M. H.; Hansen, K. B.; Jacobsen, E. N. Angew. Chem., Int. Ed. 1999, 38, 2012-2014
45. Nakano, K.; Hashimoto, S.; Nozaki, K. Chem. Sci. 2010, 1, 369-373
46. Ng Cheong Chan, Y.; Osborn, J. A. J. Am. Chem. Soc. 1990, 112, 9400-9401
47. Mccleland, B. W.; Nugent, W. A.; Finn, M. G. J. Org. Chem. 1998, 63, 6656-6666
48. Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron 2001, 57, 835-843
49. Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 1848-1855
50. ref 31a. In (b) and (c), resting-state tetramers and an active dimeric catalyst are proposed.
51. A conceptually analogous scenario, for an enzymatic reaction that exhibits overall first-order kinetics but is experimentally determined to be bimolecular, has been described: Baker, G. M.; Weng, L. J. Theor. Biol. 1992, 158, 221-229
52. Murphy, E. F.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425-3468
53. Tramšek, M.; Goreshnik, E.; Lozinšek, M.; Žemva, B. J. Fluorine Chem. 2009, 130, 1093-1098
54. Dugan, T. R.; Sun, X.; Rybak-Akimova, E. V.; Olatunji-Ojo, O.; Cundari, T. R.; Holland, P. L. J. Am. Chem. Soc. 2011, 133, 12418-12421
55. n that has been isolated and analyzed by X-ray diffraction, see: Ajiro, H.; Peretti, K. L.; Lobkovsky, E. B.; Coates, G. W. Dalton Trans. 2009, 8828-8830
56. Marzilli, L. G.; Summers, M. F.; Bresciani-Pahor, N.; Zangrando, E.; Charland, J. P.; Randaccio, L. J. Am. Chem. Soc. 1985, 107, 6880-6888
57. Zhang, Y.; Ruan, W.; Zhao, X.; Wang, H.; Zhu, Z. Polyhedron 2003, 22, 1535-1545
58. Thomas, R. M.; Widger, P. C. B.; Ahmed, S. M.; Jeske, R. C.; Hirahata, W.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2010, 132, 16520-16525
59. Kemper, S.; Hrobárik, P.; Kaupp, M.; Schlörer, N. E. J. Am. Chem. Soc. 2009, 131, 4172-4173
60. Thakur, S. S.; Li, W.-J.; Shin, C.-K.; Kim, G.-J. Chirality 2006, 18, 37-43
61. Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 120, 5840-5841
62. Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501
63. Gou, S.; Chen, X.; Xiong, Y.; Feng, X. J. Org. Chem. 2006, 71, 5732-5736
64. Mashiko, T.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 14990-14999
65. Zhang, S. Y.; Girard, C.; Kagan, H. B. Tetrahedron: Asymmetry 1995, 6, 2637-2640
66. Blackmond, D. G.; Rosner, T.; Neugebauer, T.; Reetz, M. T. Angew. Chem., Int. Ed. 1999, 38, 2196-2199
67. Bolm, C.; Muñiz, K.; Hildebrand, J. P. Org. Lett. 1999, 1, 491-493
68. Birman, V. B.; Li, X.; Han, Z. Org. Lett. 2007, 9, 37-40
69. Baidya, M.; Mayr, H. Chem. Commun. 2008, 1792-1794
70. Maji, B.; Joanesse, C.; Nigst, T. A.; Smith, A. D.; Mayr, H. J. Org. Chem. 2011, 76, 5104-5112
71. Murphy, V. J.; Hascall, T.; Chen, J. Y.; Parkin, G. J. Am. Chem. Soc. 1996, 118, 7428-7429
72. Murphy, V. J.; Rabinovich, D.; Hascall, T.; Klooster, W. T.; Koetzle, T. F.; Parkin, G. J. Am. Chem. Soc. 1998, 120, 4372-4387
73. Jasim, N. A.; Perutz, R. N. J. Am. Chem. Soc. 2000, 122, 8685-8693
74. Roe, D. C.; Marshall, W. J.; Davidson, F.; Soper, P. D.; Grushin, V. V. Organometallics 2000, 19, 4575-4582
75. Roesky, H. W.; Sotoodeh, M.; Xu, Y.; Schrumpf, F.; Noltemeyer, M. Z. Anorg. Allg. Chem. 1990, 580, 131-138
76. Fraser, S. L.; Antipin, M. Y.; Khroustalyov, V. N.; Grushin, V. V. J. Am. Chem. Soc. 1997, 119, 4769-4770
77. Pilon, M. C.; Grushin, V. V. Organometallics 1998, 17, 1774-1781
78. Basolo, F.; Matoush, W. R.; Pearson, R. G. J. Am. Chem. Soc. 1956, 78, 4883-4886
79. Kresge, A. J.; Chiang, Y. J. Phys. Chem. 1973, 77, 822-825
80. Deng, L.; Jacobsen, E. N. J. Org. Chem. 1992, 57, 4320-4323
81. Darensbourg, D. J.; Mackiewicz, R. M. J. Am. Chem. Soc. 2005, 127, 14026-14038
82. Bappert, E.; Muller, P.; Fu, G. C. Chem. Commun. 2006, 2604-2606
83. Poisson, T.; Dalla, V.; Marsais, F.; Dupas, G.; Oudeyer, S.; Levacher, V. Angew. Chem., Int. Ed. 2007, 46, 7090-7093
84. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2011, 133, 4694-4697
85. Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron. 1997, 53, 9541-9552
86. Miura, K.; Katsuki, T. Synlett. 1999, 783-785
87. Liao, S.; List, B. Angew. Chem., Int. Ed. 2010, 49, 628-631
88. Additionally, Fuiji and coworkers have observed that achiral axial ligands to (salen)Mn(IV) can amplify the stepped conformation of the chiral salen backbone: Kurahashi, T.; Hada, M.; Fujii, H. J. Am. Chem. Soc. 2009, 131, 12394-12405
89. Couturier, O.; Luxen, A.; Chatal, J.-F.; Vuillez, J.-P.; Rigo, P.; Hustinx, R. Eur. J. Nucl. Med. Mol. Imaging 2004, 31, 1182-1206
90. Kämäräinen, E.-L.; Kyllönen, T.; Nihtilä, O.; Björk, H.; Solin, O. J. Labelled Compd. Radiopharm. 2004, 47, 37-45
91. Moon, D. H.; Chi, D. Y.; Kim, D. W.; Oh, S. J.; Ryu, J. Patent WO 2006/065038 A1, June 22, 2006.
92. 18F-MISO have not been reported: Nieto, E.; Alajarín, R.; Álvarez-Builla, J.; Larrañaga, I.; Gorospe, E.; Pozo, M. Synthesis 2010, 3700
93. Olah, G. A.; Kuhn, S. J.; Dupont, J. A.; Emmons, W. D. Org. Synth. 1965, 45, 3
94. Troy Ryba, Sigma Aldrich. Personal communication, 2011.