Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles

Angewandte Chemie - International Edition

Volumn 47, Issue 22, 2008, Pages 4157-4161

  Ishimaru, Takehisa ^a   Shibata, Norio ^a   Horikawa, Takao ^a   Yasuda, Naomi ^a   Nakamura, Shuichi ^a   Toru, Takeshi ^a   Shiro, Motoo ^b  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

Allyl silanes; Asymmetric catalysis; Cinchona alkaloids; Fluorination; Silyl enol ethers

Indexed keywords

CHEMICAL REACTIONS; ENANTIOSELECTIVITY; ETHERS; FLUORINE; ORGANIC COMPOUNDS;

ALLYL SILANES; ASYMMETRIC CATALYSIS; CINCHONA ALKALOIDS; FLUORINATION; SILYL ENOL ETHERS;

SILANES;

ALKENE; ALLYLSILANE; CINCHONA ALKALOID; ETHER DERIVATIVE; FLUORINE; INDOLE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; HALOGENATION; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CINCHONA ALKALOIDS; CRYSTALLOGRAPHY, X-RAY; ETHERS; FLUORINE; HALOGENATION; INDOLES; MOLECULAR CONFORMATION; SILANES;

EID: 47049110210     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800717     Document Type: Article

References (69)

1. a) P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004;
2. b) J.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119-6146;
3. c) H. Ibrahim, A. Togni, Chem. Commun. 2004, 1147-1155;
4. d) M. Oestreich, Angew. Chem. 2005, 117, 2376-2379;
5. Angew. Chem. Int. Ed. 2005, 44, 2324-2327;
6. e) P. M. Pihko, Angew. Chem. 2006, 118, 558-561;
7. Angew. Chem. Int. Ed. 2006, 45, 544-547;
8. f) C. Bobbio, V. Gouverneur, Org. Biomol. Chem. 2006, 4, 2065-2075;
9. g) N. Shibata, J. Synth. Org. Chem. Jpn. 2006, 64, 14-24;
10. h) N. Shibata, T. Ishimaru, S. Nakamura, T. Toru, J. Fluorine Chem. 2007, 128, 469-483;
11. i) Y. Hamashima, M. Sodeoka, J. Synth. Org. Chem. Jpn. 2007, 64, 1099-1107;
12. j) V. A. Brunet, D. O'Hagan, Angew. Chem. 2008, 120, 1198-1201;
13. Angew. Chem. Int. Ed. 2008, 47, 1179-1182;
14. k) D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308-319;
15. l) S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330.
16. a) L. Hintermann, A. Togni, Angew. Chem. 2000, 112, 4530-4533;
17. Angew. Chem. Int. Ed. 2000, 39, 4359-4362;
18. b) Y. Hamashima, K. Yagi, H. Takano, L. Tamás, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 14530-14531;
19. c) R. Frantz, L. Hintermann, M. Perseghini, D. Broggini, A. Togni, Org. Lett. 2003, 5, 1709-1712;
20. d) Y. Hamashima, H. Takano, D. Hotta, M. Sodeoka, Org. Lett. 2003, 5, 3225-3228;
21. e) P. Y. Toullec, C. Bonaccorsi, A. Mezztti, A. Togni, Proc. Natl. Acad. Sci. USA 2004, 101, 5810-5814;
22. f) J.-A. Ma, D. Cahard, Tetrahedron: Asymmetry 2004, 15, 1007-1011;
23. g) Y. Hamashima, T. Suzuki, H. Takano, Y. Shimura, M. Sodeoka, J. Am. Chem. Soc. 2005, 127, 10164-10165;
24. h) H. R. Kim, D. Y. Kim, Tetrahedron Lett. 2005, 46, 3115-3117;
25. i) L. Bernardi, K. A. Jørgensen, Chem. Commun. 2005, 1324-1326;
26. j) M. Perseghini, M. Massaccesi, Y. Liu, A. Togni, Tetrahedron 2006, 62, 7180-7190;
27. k) C. Bonaccorsi, M. Althaus, C. Becker, A. Togni, A. Mezzetti, Pure Appl. Chem. 2006, 78, 391-396;
28. l) S. M. Kim, Y. K. Kang, K. S. Lee, J. Y. Mang, D. Y. Kim, Bull. Korean Chem. Soc. 2006, 27, 423-425;
29. m) S. Suzuki, H. Furuno, Y. Yokoyama, J. Inanaga, Tetrahedron: Asymmetry 2006, 17, 504-507;
30. n) Y. Hamashima, T. Suzuki, H. Takano, Y. Shimura, Y. Tsuchiya, K. Moriya, T. Goto, M. Sodeoka, Tetrahedron 2006, 62, 7168-7179;
31. o) M. Althaus, C. Becker, A. Togni, A. Mezzetti, Organometallics 2007, 26, 5902-5911;
32. p) T. Suzuki, T. Goto, Y. Hamashima, M. Sodeoka, J. Org. Chem. 2007, 72, 246-250;
33. q) K. Shibatomi, Y. Tsuzuki, S. Nakata, Y. Sumikawa, S. Iwasa, Synlett 2007, 551-554;
34. r) K. Kang, M. J. Cho, S. M. Kim, D. Y. Kim, Synlett 2007, 1135-1138;
35. s) K. Moriya, Y. Hamashima, M. Sodeoka, Synlett 2007, 1139-1142;
36. t) T. Suzuki, Y. Hamashima, M. Sodeoka, Angew. Chem. 2007, 119, 5531-5535;
37. Angew. Chem. Int. Ed. 2007, 46, 5435-5439.
38. a) N. Shibata, T. Ishimaru, T. Nagai, J. Kohno, T. Toru, Synlett 2004, 1703-1706;
39. b) N. Shibata, J. Kohno, K. Takai, T. Ishimaru, S. Nakamura, T. Toru, S. Kanemasa, Angew. Chem. 2005, 117, 4276-4279;
40. Angew. Chem. Int. Ed. 2005, 44, 4204-4207;
41. c) N. Shibata, H. Yasui, S. Nakamura, T. Toru, Synlett 2007, 1153-1157;
42. d) D. S. Reddy, N. Shibata, J. Nagai, S. Nakamura, T. Toru, S. Kanemasa, Angew. Chem. 2008, 120, 170-174;
43. Angew. Chem. Int. Ed. 2008, 47, 164-168.
44. a) D. Enders, M. R. M. Hüttl, Synlett 2005, 991-993;
45. b) M. Marigo, D. Fielenbach, A. Braunton, A. Kjærsgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769-3772;
46. Angew. Chem. Int. Ed. 2005, 44, 3703-3706;
47. c) D. D. Steiner, N. Mase, C. F. Barbas III, Angew. Chem. 2005, 117, 3772-3776;
48. Angew. Chem. Int. Ed. 2005, 44, 3706-3710;
49. d) T. D. Beeson, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 8826-8828;
50. e) S. Brandes, B. Niess, M. Bella, A. Prieto, J. Overgaard, K. A. Jørgensen, Chem. Eur. J. 2006, 12, 6039-6052.
51. a) N. Shibata, E. Suzuki, Y. Takeuchi, J. Am. Chem. Soc. 2000, 122, 10728-10729;
52. b) N. Shibata, E. Suzuki, T. Asahi, M. Shiro, J. Am. Chem. Soc. 2001, 123, 7001-7009;
53. c) N. Shibata, T. Ishimaru, E. Suzuki, K. L. Kirk, J. Org. Chem. 2003, 68, 2494-2497;
54. d) N. Shibata, T. Ishimaru, M. Nakamura, T. Toru, Synlett 2004, 2509-2512.
55. a) D. Cahard, C. Audouard, J.-C. Plaquevent, N. Roques, Org. Lett. 2000, 2, 3699-3701;
56. b) B. Mohar, J. Baudoux, J.-C. Plaquevent, D. Cahard, Angew. Chem. 2001, 113, 4339-4341;
57. Angew. Chem. Int. Ed. 2001, 40, 4214-4216;
58. c) D. Cahard, C. Audouard, J.-C. Plaquevent, L. Toupet, N. Roques, Tetrahedron Lett. 2001, 42, 1867-1869;
59. d) C. Baudequin, J.-C. Plaquevent, C. Audouard, D. Cahard, Green Chem. 2002, 4, 584-586;
60. e) C. Baudequin, J.-F. Loubassou, J.-C. Plaquevent, D. Cahard, J. Fluorine Chem. 2003, 122, 189-193;
61. f) L. Zoute, C. Audouard, J.-C. Plaquevent, D. Cahard, Org. Biomol. Chem. 2003, 1, 1833-1834;
62. g) B. Mohar, D. Sterk, L. Ferron, D. Cahard, Tetrahedron Lett. 2005, 46, 5029-5031;
63. h) B. Greedy, J. M. Paris, T. Vidal, V. Gouverneur, Angew. Chem. 2003, 115, 3413-3416;
64. Angew. Chem. Int. Ed. 2003, 42, 3291-3294;
65. i) M. Wang, B. M. Wang, L. Shi, Y. Q. Tu, C.-A. Fan, S. H. Wang, X. D. Hu, S. Y. Zhang, Chem. Commun. 2005, 5580-5582;
66. j) E. Ramírez, D. P. Huber, A. Togni, Synlett 2007, 1143-1147.
67. T. Fukuzumi, N. Shibata, M. Sugiura, S. Nakamura, T. Toru, J. Fluorine Chem. 2006, 127, 548-551.
68. M. W. Justik, G. F. Koser, Molecules 2005, 10, 217-225.
69. P. Hawawasom, N. A. Meanwell, V. K. Gribkoff, S. I. Dworetzky, C. G. Boissard, Bioorg. Med. Chem. Lett. 1997, 7, 1255-1260.