SPANamine derivatives in the catalytic asymmetric α-fluorination of β-keto esters

Tetrahedron Asymmetry

Volumn 22, Issue 14-15, 2011, Pages 1490-1498

  Jacquet, Olivier ^a,b   Clément, Nicolas D ^b   Freixa, Zoraida ^b,c   Ruiz, Aurora ^a   Claver, Carmen ^a   Van Leeuwen, Piet W N M ^b  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^c UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA KETOESTER DERIVATIVE; ESTER DERIVATIVE; NICKEL CHLORIDE; SPANAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 80054946417     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.08.023     Document Type: Article

References (55)

1. For review see: S. France, A. Weatherwax, and T. Lectka Eur. J. Org. Chem. 2005 475
2. M. Oestreich Angew. Chem., Int. Ed. 44 2005 2324
3. G.K.S. Prakash, and P. Beier Angew. Chem., Int. Ed. 45 2006 2172
4. C. Bobbio, and V. Gouverneur Org. Biomol. Chem. 4 2006 2065
5. N. Shibata, T. Ishimaru, S. Nakamura, and T. Toru J. Fluorine Chem. 128 2007 469
6. V.A. Brunet, and D. O'Hagan Angew. Chem., Int. Ed. 47 2008 1179
7. J.-A. Ma, and D. Cahard Chem. Rev 108 2008 1
8. M. Ueda, T. Kano, and K. Maruoka Org. Biomol. Chem. 7 2009 2005
9. D. Cahard, X. Xu, S. Couve-Bonnaire, and X. Pannecoucke Chem. Soc. Rev. 2010 558
10. G. Valero, X. Companyó, and R. Rios Chem. Eur. J. 17 2011 2018
11. D.Y. Kim, and E.J. Park Org. Lett. 4 2002 545
12. X. Wang, Q. Lan, S. Shirakawa, and K. Maruoka Chem. Commun. 46 2010 321
13. N. Shibata, T. Ishimaru, T. Nagai, J. Kohno, and T. Toru Synlett 2004 1703
14. J.-A. Ma, and D. Cahard Tetrahedron: Asymmetry 15 2004 1007
15. J.-A. Ma, and D. Cahard J. Fluorine Chem. 125 2004 1357
16. N. Shibata, J. Kohno, K. Takai, T. Ishimaru, S. Nakamura, T. Toru, and S. Kanemasa Angew. Chem., Int. Ed. 44 2005 4204
17. K. Shibatomi, Y. Tsuzuki, S.-I. Nakata, Y. Sumikawa, and S. Iwasa Synlett 2007 551
18. N. Shibata, H. Yasui, S. Nakamura, and T. Toru Synlett 2007 1153
19. M. Althaus, C. Becker, A. Togni, and A. Mezzetti Organometallics 26 2007 5902
20. Shibatomi, K.; Jpn Kokai Tokkyo Koho 2008, 1pp, JP 2006-19502220060718.
21. K. Shibatomi, Y. Tsuzuki, and S. Iwasa Chem. Lett. 37 2008 1098
22. M. Frings, and C. Bolm Eur. J. Org. Chem. 24 2009 4085
23. A. Assalit, T. Billard, S. Chambert, B.R. Langlois, Y. Queneau, and D. Coe Tetrahedron: Asymmetry 20 2009 593
24. S.H. Kang, and D.Y. Kim Adv. Synth. Catal. 352 2010 2783
25. X. Sala, E.J. García Suárez, Z. Freixa, J. Benet-Bulchholz, and P.W.N.M. Van Leeuwen Eur. J. Org. Chem. 2008 6197
26. While this manuscript was in preparation a publication appeared in which a SPANbox was reported and successfully applied in asymmetric oxygenation: J. Li, G. Chen, Z. Wang, R. Zhang, X. Zhang, and K. Ding Chem. Sci. 2 2011 1141
27. Y. Hamashima, K. Yagi, H. Takano, L. Tamas, and M. Sodeoka J. Am. Chem. Soc. 124 2002 1453
28. Y. Hamashima, H. Takano, D. Hotta, and M. Sodeoka Org. Lett. 5 2003 3225
29. Sodeoka, M.; Hamashima, Y.; Jpn Kokai Tokkyo Koho 2004, JP 2004010555.
30. P. Toullec, C. Bonaccorsi, A. Mezzetti, and A. Togni Proc. Nat. Am. Sci. 101 2004 5810
31. Y. Hamashima, T. Suzuki, H. Takano, Y. Shimura, Y. Tsuchiya, K.-I. Moriya, T. Goto, and M. Sodeoka Tetrahedron 62 2006 7168
32. S. Suzuki, H. Furuno, Y. Yokohama, and J. Inanaza Tetrahedron: Asymmetry 17 2006 504
33. N.R. Lee, S.M. Kim, and D.Y. Kim Bull. Kor. Chem. Soc. 30 2009 829
34. R.D. Chambers, T. Nakano, T. Okazoe, and G. Sandford J. Fluorine Chem. 130 2009 792
35. T. Ishimaru, N. Shibata, D.S. Reddy, T. Horikawa, S. Nakamura, and T. Toru Beilstein. J. Org. Chem. 4 2008 16
36. D.S. Reddy, N. Shibata, T. Horikawa, S. Suzuki, S. Nakamura, T. Toru, and S. Motoo Chem. Asian J. 4 2009 1411
37. D. Enders, and M.R.M. Hüttl Synlett 2005 991
38. D.D. Steiner, N. Mase, and C.F. Barbas Angew. Chem., Int. Ed. 44 2005 3706
39. M. Marigo, D. Fielenbach, A. Braunton, A. Kjœrsgaard, and K.A. Jørgensen Angew. Chem., Int. Ed. 44 2005 3703
40. S. Brandes, B. Niess, M. Bella, A. Prieto, A. Kjœrsgaard, and K.A. Jørgensen Chem. Eur. J. 2006 6039
41. T. Beeson, and D.W.C. MacMillan J. Am. Chem. Soc. 127 2005 8826
42. Y. Huang, A.M. Walji, C.H. Larsen, and D.W.C. MacMillan J. Am. Chem. Soc. 127 2005 15051
43. N. Shibata, E. Suzuki, and Y. Takeuchi J. Am. Chem. Soc. 122 2000 10728
44. N. Shibata, E. Suzuki, T. Asahi, and M. Shiro J. Am. Chem. Soc. 123 2001 7001
45. N. Shibata, T. Ishimaru, E. Suzuki, and K.L. Kirk J. Org. Chem. 68 2003 2494
46. N. Shibata, T. Ishimaru, S. Nakamura, and T. Toru Synlett 2004 2509
47. M. Wang, B.M. Wang, L. Shi, Y.Q. Tu, C.-A. Fan, S.H. Wang, X.D. Hu, and S.Y. Zhang Chem. Commun. 44 2005 5580
48. T. Fukuzumi, N. Shibata, M. Sugiura, S. Nakamura, and T. Toru J. Fluorine Chem. 127 2006 548
49. J. Ramirez, D.P. Huber, and A. Togni Synlett 2007 1143
50. T. Ishimaru, N. Shibata, T. Horikawa, N. Yasuda, S. Nakamura, T. Toru, and M. Shiro Angew. Chem., Int. Ed. 47 2008 4157
51. M.E. Bunnage, S.G. Davies, R.M. Parkin, P.M. Roberts, A.D. Smith, and J.M. Withey Org. Biomol. Chem. 2 2004 3337
52. T.A. Moss, D.R. Fenwick, and D.J. Dixon J. Am. Chem. Soc. 130 2008 10076
53. D.S. Brown, B.A. Marples, P. Smith, and L. Walton Tetrahedron 51 1995 5587
54. T.A. Moss, A. Alba, D. Hepworth, and D.J. Dixon Chem. Commun. 2008 2474
55. K. Khumtaveeporn, A. Ullmann, K. Matsumoto, B.G. Davis, and J.B. Jones Tetrahedron: Asymmetry 12 2001 249