Enantioselective organocatalytic conjugate addition of fluorocarbon nucleophiles to α,β-unsaturated aldehydes

Chemistry - A European Journal

Volumn 15, Issue 39, 2009, Pages 10013-10017

  Ullah, Farman ^a   Zhao, Gui Ling ^a   Deiana, Luca ^a   Zhu, Mingzhao ^a   Dziedzic, Pawel ^a   Ibrahem, Ismail ^a   Hammar, Peter ^b   Sun, Junliang ^a   Córdova, Armando ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Aldehydes; Asymmetric catalysis; Chemoselectivity; Fluorine; Organocatalysis

Indexed keywords

ACID ADDITIVES; ALCOHOL DERIVATIVES; ASYMMETRIC CATALYSIS; CHEMOSELECTIVITY; CHIRAL AMINES; CONJUGATE ADDITION; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; FLUORINE ATOMS; HIGH ENANTIOSELECTIVITY; IMINIUM; IN-SITU; ORGANOCATALYSIS; ORGANOCATALYTIC; QUATERNARY CARBON; REACTION CONDITIONS; STEREOCENTERS; UNSATURATED ALDEHYDES;

ADDITION REACTIONS; ALDEHYDES; AMINES; CATALYSIS; ELECTRON TRANSITIONS; ETHANOL; FLUORINE; NUCLEOPHILES; ORGANIC POLYMERS; RATE CONSTANTS; REACTION KINETICS; STEREOSELECTIVITY; TOLUENE;

ENANTIOSELECTIVITY;

1 FLUORO BIS(PHENYLSULFONYL)METHANE; 1-FLUORO-BIS(PHENYLSULFONYL)METHANE; ALDEHYDE; ALKENE; FLUOROCARBON; SULFONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; ALKENES; CATALYSIS; FLUOROCARBONS; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONES;

EID: 70349655526     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901260     Document Type: Article

References (101)

1. a) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Eds.: R. Filler, Y Kobayashim, L. M. Yagupolskii), Elsevier, Amsterdam, 1993;
2. b) P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004;
3. T. Hiyama in Organofluorine Compounds: Chemistry and Applications, Springer, Berlin, 2000.
4. a) K. Müller, C. Faeh, D. Diederich, Science 2007, 317, 1881;
5. b) S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320.
6. a) G. L. Grunewald, T. M. Caldwell, Q. Li, M. Slavica, K. R. Criscione, R. T. Borchardt, W. Wang, J. Med. Chem. 1999, 42, 3588;
7. b) J. Kollonitsch, A. A. Patchett, S. Marburg, A. L. Maycock, L. M. Perkins, G. A. Doldouras, D. E. Duggan, S. D. Aster, Nature 1978, 274, 906;
8. R. B. Silverman, S. M. Nanavati, J. Med. Chem. 1990, 33, 931.
9. a) L. Hintermann, A. Togni, Angew. Chem. 2000, 112, 4530;
10. Angew. Chem. Int. Ed. 2000, 39, 4359.
11. a) H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147;
12. b)J. A. Ma, D. Cahard, Chem. Soc. Rev. 2004, 33, 6119;
13. c) C. Bobbio, V. Gouverneur, Org. Biomol. Chem. 2006, 4, 2065;
14. d) M. Oestreich, Angew. Chem. 2005, 117, 2376;
15. Angew. Chem. Int. Ed. 2005, 44, 2324;
16. e) P. M. Pihko, Angew. Chem. 2006,118, 558;
17. Angew. Chem. Int. Ed. 2006, 45, 544.
18. For selected examples of the use of NFSI, see: a) Y. Hamashima, K. Yagi, H. Takáno, L. Tamás, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 14530;
19. b) D. Y Kim, E. J. Park, Org. Lett. 2002, 4, 545;
20. c) P. Y. Toullec, C. Bonacorsi, A. Mezzeti, A. Togni, Proc. Natl. Acad. Sci. USA 2004, 101, 5810;
21. d) T. Suzuki, Y. Hamashima, M. Sodeoka, Angew. Chem. 2007, 119, 5531;
22. Angew. Chem. Int. Ed. 2007, 46, 5435;
23. e) D. S. Reddy, N. Shibata, J. Nagai, S. Nakamura, T. Toru, S. Kanemasa, Angew. Chem. 2008, 120, 170;
24. Angew. Chem. Int. Ed. 2008, 47, 164.
25. For selected organocatalytic examples, see: a) N. Shibata, E. Suzuki, Y. Takeuchi, J. Am. Chem. Soc. 2000, 122, 10728;
26. b) B. Greedy, J. M. Paris, T. Vidal, V. Gouverneur, Angew. Chem. 2003, 115, 3413;
27. Angew. Chem. Int. Ed. 2003, 42, 3291;
28. c) D. Enders, M. R. M. Hüttl, Synlett 2005, 0991;
29. d) M. Marigo, D. Fielenbach, A. Braunton, A. Kjoersgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769;
30. Angew. Chem. Int. Ed. 2005, 44, 3703;
31. e) D. D. Steiner, N. Mase, C. F. Barbas III, Angew. Chem. 2005, 117, 3772;
32. Angew. Chem. Int. Ed. 2005, 44, 3706;
33. f) T. D. Beeson, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 8826;
34. g) S. Brandes, B. Niess, M. Bella, A. Prieto, J. Overgaard, K. A. Jørgensen, Chem. Eur. J. 2006, 12, 6039;
35. h) T. Ishimaru, N. Shibata, T. Horikawa, N. Yasuda, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 4225;
36. Angew. Chem. Int. Ed. 2008, 47, 4157.
37. a) T. Furukawa, N. Shibata, S. Mizuta, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 8171;
38. Angew. Chem. Int. Ed. 2008, 47, 8051;
39. b) G. K. S. Prakash, F. Wang, T. Stewart, T. Mathew, G. A. Olah, Proc. Natl. Acad. Sci. USA 2009, 106, 4090; during the preparation of this manuscript two elegant papers appeared describing the addition of 2-fluoro-β- ketoesters to electrophiles employing bicyclic guanidines and cinchona alkaloid catalysts, respectively:
40. c) Z. Jiang, Y. Pan, Y. Zhao, T. Ma, R. Lee, Y. Yang, K.-W. Huang, M. W. Wong, C.-H. Tan, Angew. Chem. 2009,121, 3681;
41. Angew. Chem. Int. Ed. 2009, 48, 3627;
42. d) H. Li, S. Zhang, C. Yu, X. Song, W. Wang, Chem. Commun. 2009, 2136.
43. a) T. Fukuzumi, N. Shibata, M. Sugiura, H. Yasui, S. Nakamura, T. Toru, Angew. Chem. 2006, 118, 5095;
44. Angew. Chem. Int. Ed. 2006, 45, 4973;
45. b) S. Mizuta, N. Shibata, Y. Goto, T. Furukawa, S. Nakamura, T. Toru, J. Am. Chem. Soc. 2007, 129, 6394.
46. a) G. K. S. Prakash, S. Chako, S. Alconcel, T. Stewart, T. Mathew, G. A. Olah, Angew. Chem. 2007, 119, 5021;
47. Angew. Chem. Int. Ed. 2007, 46, 4933;
48. b) G. K. S. Prakash, X. Zhao, S. Chacko, F. Wang, H. Vaghoo, G. A. Olah, Beilstein J. Org. Chem. 2008, 4: 1.
49. a) C. Ni, Y Li, J. Hu, J. Org. Chem. 2006, 71, 6289;
50. b) C Ni, L. Zhang, J. Hu, J. Org. Chem. 2008, 73, 5699.
51. For selected reviews, see: a) A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2004;
52. b) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471;
53. c) A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416;
54. d) M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001.
55. For selected examples, see: a) K. A. Ahrendt, C. J. Borths, D.W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243;
56. b) A. B. Northrup, D.W. C MacMillan, J. Am. Chem. Soc. 2002, 124, 2458;
57. c) R. K. Kunz, D.W.C. MacMillan, J. Am. Chem. Soc. 2005, 127, 3240;
58. d) W. S. Jen, J. J. M. Wiener, D. W. C MacMillan, J. Am. Chem. Soc. 2000, 122, 9874;
59. e)N. Halland, P. S. Aburell, K. A. Jørgensen, Angew. Chem. 2004, 116, 1292;
60. Angew. Chem. Int. Ed. 2004, 43, 1272;
61. f) S. Brandau, A. Landa, J. Franzen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411;
62. Angew. Chem. Int. Ed. 2006, 45, 4305;
63. g) A. Carlone, S. Cabrera, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1119;
64. Angew. Chem. Int. Ed. 2007, 46, 1101, and references therein;
65. h) A. Carlone, M. Marigo, C. North, A. Landa, K. A. Jørgensen, Chem. Commun. 2006, 4928;
66. i) H. Gotoh, R. Masui, H. Ogino, M . Shoji, Y. Hayashi, Angew. Chem. 2006,118, 7007;
67. Angew. Chem. Int. Ed. 2006, 45, 6853;
68. j) S. Hanessian, V. Pham, Org. Lett. 2000,2, 2975.
69. For selected examples of hydrido nucleophiles, see: a) J. W. Yang, M. T. Hechevarria Fonseca, N Vignola, B. List, Angew. Chem. 2005, 117, 110;
70. Angew. Chem. Int. Ed. 2005, 44, 108;
71. b) S. G. Guellet, J. B. Tuttle, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 32;
72. c) S. Mayer, B. List, Angew. Chem. 2006, 118, 4299;
73. Angew. Chem. Int. Ed. 2006, 45, 4193;
74. d) R. M. Wilson, W. S. Jen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127,11616;
75. e) G. L. Zhao, A. Córdova, Tetrahedron Lett. 2006, 47, 7417; for selected examples of nitrogen nucleophiles, see:
76. f)Y. K. Chen, M. Yoshida, D.W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 9328;
77. g)I. Ibrahem, R. Rios, J. Vesely, G.-L. Zhao, A. Cordova, Chem. Commun. 2006, 849;
78. h) H. Sundén, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Córdova, Adv. Synth. Catal. 2007, 349, 827;
79. i) J. Vesely, I. Ibrahem, R. Rios, G. L. Zhao, Y. Xu, A. Córdova, Tetrahedron Lett. 2007, 48, 2193;
80. j)P. Dinér, M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 1983;
81. k) J. Vesely, I. Ibrahem, G.-L. Zhao, R. Rios, A. Córdova, Angew. Chem. 2007,119, 792;
82. Angew. Chem. Int. Ed. 2007, 46, 778;
83. G. L. Zhao, R. Rios, J. Vesely, L. Eriksson, A. Córdova, Angew. Chem. 2008,120, 8596;
84. Angew. Chem. Int. Ed. 2008, 47, 8468; for selected examples of sulfur nucleophiles see :
85. M. Marigo, T. Schulte, J. Franzen, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 15710;
86. n) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc. 2006, 128, 10354;
87. o) R. Rios, H. Sunden, I. Ibrahem, G. L. Zhao, L. Eriksson, A. Córdova, Tetrahedron Lett. 2006, 47, 8547;
88. p) S. Brandau, E. Maerten, K. A. Jørgensen, J. Am. Chem. Soc. 2006,128, 14986. For selected examples of oxygen nucleophiles, see :
89. q) S. Bertelsen, P. Dinér, R. L. Johansen, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 1536;
90. r) T. Govender, L. Hojabri, F. M. Moghaddam, P. I. Arvidsson, Tetrahedron: Asymmetry 2006, 17, 1763;
91. s)H. Sunden, I. Ibrahem, G. L. Zhao, L. Eriksson, A. Córdova, Chem. Eur. J. 2007, 13, 574;
92. t) A. Pohjakallio, P. M. Pihko, Chem. Eur. J. 2009, 15, 3960; for selected examples of phosphorus nucleophiles, see:
93. u) I. Ibrahem, R. Rios, J. Veselý, P. Hammar, L. Eriksson, F. Himo, A. Córdova, Angew. Chem. 2007, 119, 4591;
94. Angew. Chem. Int. Ed. 2007, 46, 4507;
95. A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588;
96. Angew. Chem. Int. Ed. 2007, 46, 4504.
97. See reference [7d] and a) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
98. Angew. Chem. Int. Ed. 2005, 44, 4212;
99. b) for a review, see: A. Mielgo, C Palomo, Chem. Asian J. 2008, 3, 922.
100. CCDC 730063 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data-request/cif.
101. After the submission of our manuscript a similar paper describing the FBSM reaction appeared, see: A.-M. Alba, X. Companyo, A. Moyano, R. Rios, Chem. Eur. J. 2009, 15, 7035.