Catalytic asymmetric Mannich-type reactions of fluorinated ketoesters with N-Boc aldimines in the presence of chiral palladium complexes

Tetrahedron Letters

Volumn 52, Issue 18, 2011, Pages 2356-2358

  Kang, Young Ku ^a   Kim, Dae Young ^a  

^a Soonchunhyang University   (South Korea)

Author keywords

Fluoro ketoesters; Aldimines; Asymmetric catalysis; Chiral palladium catalysts; Mannich reaction

Indexed keywords

ESTER DERIVATIVE; IMINE; MANNICH BASE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; FLUORINATION;

EID: 79953278559     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.087     Document Type: Article

References (96)

1. M. Hudlicky, and A.E. Pavlath Chemistry of Organic Fluorine Compounds II 1995 American Chemical Society Washington, DC
2. K.L.J. Kirk J. Fluorine Chem. 127 2006 1013
3. C. Isanobor, and D. O'Hagan J. Fluorine Chem. 127 2006 303
4. K. Muller, C. Faeh, and F. Diederich Science 317 2007 1881
5. K.L. Kirk Org. Process Res. Dev. 12 2008 305
6. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320
7. T. Hiyama, K. Kanie, T. Kusumoto, Y. Morizawa, and M. Shimizu Organofluorine Compounds: Chemistry and Applications 2000 Springer-Verlag Berlin
8. V.A. Soloshonok, Enantiocontrolled Synthesis of Fluoro-organic Compounds 1999 John Wiley & Sons Chichester
9. P. Bravo, and G. Resnati Tetrahedron: Asymmetry 1 1990 661
10. P.V. Ramachandran, Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions ACS Symposium Series 746 2000 American Chemical Society Washington, DC
11. For reviews, see: K. Mikami, Y. Itoh, and M. Yamanaka Chem. Rev. 104 2004 1
12. H. Ibrahim, and A. Togni Chem. Commun. 2004 1147
13. J.-A. Ma, and D. Cahard Chem. Rev. 108 2008 PR1
14. S. France, A. Weatherwax, and T. Lectka Eur. J. Org. Chem. 2005 475
15. M. Oestreich Angew. Chem., Int. Ed. 44 2005 2324
16. P.M. Pihko Angew. Chem., Int. Ed. 45 2006 544
17. G.K.S. Prakash, and P. Beier Angew. Chem., Int. Ed. 45 2006 2172
18. C. Bobbio, and V. Gouverneur Org. Biomol. Chem. 4 2006 2065
19. N. Shibata, T. Ishimaru, S. Nakamura, and T. Toru J. Fluorine Chem. 128 2007 469
20. V.A. Brunet, and D. O'Hagan Angew. Chem., Int. Ed. 47 2008 1179
21. R. Smits, C.D. Cadicamo, K. Burger, and B. Koksch Chem. Soc. Rev. 37 2008 1727
22. Y.K. Kang, and D.Y. Kim Curr. Org. Chem. 14 2010 917
23. For recent selected examples of catalytic asymmetric fluorinations of active methines, see: L. Hintermann, and A. Togni Angew. Chem., Int. Ed. 39 2000 4359
24. D.Y. Kim, and E.J. Park Org. Lett. 4 2002 545
25. Y. Hamashima, K. Yagi, H. Takano, L. Tamás, and M. Sodeoka J. Am. Chem. Soc. 124 2002 14530
26. J.-A. Ma, and D. Cahard Tetrahedron: Asymmetry 15 2004 1007
27. N. Shibata, T. Ishimaru, T. Nagai, J. Kohno, and T. Toru Synlett 2004 1703
28. L. Bernardi, and K.A. Jørgensen Chem. Commun. 2005 1324
29. S.M. Kim, H.R. Kim, and D.Y. Kim Org. Lett. 7 2005 2309
30. H.R. Kim, and D.Y. Kim Tetrahedron Lett. 46 2005 3115
31. T. Ishimaru, N. Shibata, T. Horikawa, N. Yasuda, S. Nakamura, T. Toru, and M. Shiro Angew. Chem., Int. Ed. 47 2008 4157
32. N.R. Lee, S.M. Kim, and D. Kim Bull. Korean Chem. Soc. 30 2009 829
33. S.H. Kang, and D.Y. Kim Adv. Synth. Catal. 352 2010 2783
34. For asymmetric Michael-type reactions of α-fluoromalonates, see: D.Y. Kim, S.M. Kim, K.O. Koh, and J.Y. Mang Bull. Korean Chem. Soc. 24 2003 1425
35. P.J. Nichols, J.A. DeMattei, B.R. Barnett, N.A. LeFur, T.-H. Chuang, A.D. Piscopio, and K. Koch Org. Lett. 8 2006 1495
36. B.K. Kwon, S.M. Kim, and D.Y. Kim J. Fluorine Chem. 130 2009 759
37. X. Companyo, M. Hejnova, M. Kamlar, J. Vesely, A. Moyano, and R. Rios Tetrahedron Lett. 50 2009 5051
38. S.H. Kang, and D.Y. Kim Bull. Korean Chem. Soc. 30 2009 1439
39. For asymmetric Michael-type reactions of α-fluoro-β- ketoesters, see: M. Nakamura, A. Hajra, K. Endo, and E. Nakamura Angew. Chem., Int. Ed. 44 2005 7248
40. R. He, X. Wang, T. Hashimoto, and K. Maruoka Angew. Chem., Int. Ed. 47 2008 9466
41. J.Y. Mang, D.G. Kwon, and D.Y. Kim J. Fluorine Chem. 130 2009 259
42. X. Han, J. Luo, C. Liu, and Y. Lu Chem. Commun. 2009 2044
43. H. Li, S. Zhang, C. Yu, X. Song, and W. Wang Chem. Commun. 2009 2136
44. Y. Oh, S.M. Kim, and D.Y. Kim Tetrahedron Lett. 50 2009 4674
45. T. Ishimaru, S. Ogawa, E. Tokunaga, S. Nakamura, and N. Shibata J. Fluorine Chem. 130 2009 1049
46. H.-F. Cui, Y.-Q. Yang, Z. Chai, P. Li, C.-W. Zheng, and S.-Z. Zhu J. Org. Chem. 75 2010 117
47. For asymmetric reactions using fluorobis(phenysulfonyl)methane derivatives, see: T. Fukuzumi, N. Shibata, M. Sugiura, H. Yasui, S. Nakamura, and T. Toru Angew. Chem., Int. Ed. 45 2006 4973
48. S. Mizuta, N. Shibata, Y. Goto, T. Furukawa, S. Nakamura, and T. Toru J. Am. Chem. Soc. 129 2007 6394
49. T. Furukawa, N. Shibata, S. Mizuta, S. Nakamura, T. Toru, and M. Shiro Angew. Chem., Int. Ed. 47 2008 8051
50. H.W. Moon, M.J. Cho, and D.Y. Kim Tetrahedron Lett. 50 2009 4896
51. T. Furukawa, Y. Goto, J. Kawazoe, E. Tokunaga, S. Nakamura, Y. Yang, H. Du, A. Kakehi, M. Shiro, and N. Shibata Angew. Chem., Int. Ed. 49 2010 1642
52. For selected recent reviews, see: A. Cordova Acc. Chem. Res. 37 2004 102
53. M.M.B. Marques Angew. Chem., Int. Ed. 45 2006 348
54. A. Ting, and S.E. Schaus Eur. J. Org. Chem. 2007 5797
55. J.M.M. Verkade, L.J.C. van Hemert, P.J.L.M. Quaedflieg, and F.P.J.T. Rutjes Chem. Soc. Rev. 37 2008 29
56. M. Hatano, and K. Ishihara Synthesis 2010 3785
57. Selected examples of Mannich-type reactions of enolates, see: M. Sikert, and C. Schneider Angew. Chem., Int. Ed. 47 2008 3631
58. J. Itoh, K. Fuchibe, and T. Akiyama Synthesis 2008 1319
59. S. Kobayashi, R. Yazaki, K. Seki, and M. Ueno Tetrahedron 63 2007 8425
60. K. Saruhashi, and S. Kobayashi J. Am. Chem. Soc. 128 2006 11232
61. S. Kobayashi, M. Ueno, S. Saito, Y. Mizuki, H. Ishitani, and Y. Yamashita Proc. Natl. Acad. Sci. U.S.A. 101 2004 5476
62. T. Akiyama, J. Itoh, K. Yokota, and K. Fuchibe Angew. Chem., Int. Ed. 43 2004 1566
63. A.G. Wenzel, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 12964
64. Y. Hamashima, N. Sasamoto, N. Umebayashi, and M. Sodeoka Chem. Asian J. 3 2008 1443
65. Z. Chen, H. Morimoto, S. Matsunaga, and M. Shibasaki J. Am. Chem. Soc. 130 2008 2170
66. S. Kobayashi, T. Gustafsson, Y. Shimizu, H. Kiyohara, and R. Matsubara Org. Lett. 8 2006 4923
67. Y. Hamashima, N. Sasamoto, D. Hotta, H. Somei, N. Umebayashi, and M. Sodeoka Angew. Chem., Int. Ed. 44 2005 1525
68. Y.K. Kang, and D.Y. Kim J. Org. Chem. 74 2009 5734
69. J.H. Lee, and D.Y. Kim Adv. Synth. Catal. 351 2009 1779
70. E.J. Kim, Y.K. Kang, and D.Y. Kim Bull. Korean Chem. Soc. 30 2009 1437
71. J.H. Lee, and D.Y. Kim Synthesis 2010 1860
72. X. Han, J. Kwiatkowski, F. Xue, K.-W. Huang, and Y. Lu Angew. Chem., Int. Ed. 48 2009 7604
73. Z. Jiang, Y. Pan, Y. Zhao, T. Ma, R. Lee, Y. Yang, K.-W. Huang, M.W. Wong, and C.-H. Tan Angew. Chem., Int. Ed. 48 2009 3627
74. Y. Pan, Y. Zhao, T. Ma, Y. Yang, H. Liu, Z. Jiang, and C.-H. Tan Chem. Eur. J. 16 2010 779
75. S.J. Yoon, Y.K. Kang, and D.Y. Kim Synlett 2011 420
76. D.Y. Kim, S.C. Huh, and S.M. Kim Tetrahedron Lett. 42 2001 6299
77. D.Y. Kim, and S.C. Huh Tetrahedron 57 2001 8933
78. E.J. Park, M.H. Kim, and D.Y. Kim J. Org. Chem. 69 2004 6897
79. J.Y. Mang, and D.Y. Kim Bull. Korean Chem. Soc. 29 2008 2091
80. Y.K. Kang, and D.Y. Kim Bull. Korean Chem. Soc. 29 2008 2093
81. S.M. Kim, J.H. Lee, and D.Y. Kim Synlett 2008 2659
82. S.H. Jung, and D.Y. Kim Tetrahedron Lett. 49 2008 5527
83. D.Y. Kim Bull. Korean Chem. Soc. 29 2008 2036
84. J.Y. Mang, D.G. Kwon, and D.Y. Kim Bull. Korean Chem. Soc. 30 2009 249
85. B.K. Kwon, and D.Y. Kim Bull. Korean Chem. Soc. 30 2009 1441
86. Y.K. Kang, S.M. Kim, and D.Y. Kim J. Am. Chem. Soc. 132 2010 11847
87. Y.K. Kang, and D.Y. Kim Tetrahedron Lett. 47 2006 4565
88. Y.K. Kang, M.J. Cho, S.M. Kim, and D.Y. Kim Synlett 2007 1135
89. M.J. Cho, Y.K. Kang, N.R. Lee, and D.Y. Kim Bull. Korean Chem. Soc. 28 2007 2191
90. S.M. Kim, Y.K. Kang, M.J. Cho, J.Y. Mang, and D.Y. Kim Bull. Korean Chem. Soc. 28 2007 2435
91. J.H. Lee, H.T. Bang, and D.Y. Kim Synlett 2008 1821
92. S.H. Kang, Y.K. Kang, and D.Y. Kim Tetrahedron 65 2009 5676
93. K. Li, P.N. Horton, M.B. Hursthouse, and K.K. Hii J. Organomet. Chem. 665 2003 250
94. For a aquapalladium complex, see T. Shimada, G.B. Bajracharya, and Y. Yamamoto Eur. J. Org. Chem. 2005 59 and references cited therein
95. J. Vicente, and A. Arcas Coord. Chem. Rev. 249 2005 1135
96. R = 14.9 min (major), 99% ee.