Copper(II)-catalyzed enantioselective fluorination of β-keto esters using chiral spiro oxazoline ligands

Synlett

Volumn 24, Issue 3, 2013, Pages 375-378

  Narayama, Akira ^a   Shibatomi, Kazutaka ^a   Soga, Yoshinori ^a   Muto, Tsubasa ^a   Iwasa, Seiji ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

asymmetric catalysis; chiral ligands; fluorination; Lewis acid; spiro compounds

Indexed keywords

ALPHA ALKYL BETA KETO ESTER DERIVATIVE; COPPER COMPLEX; CUPRIC ION; ESTER DERIVATIVE; LEWIS ACID; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; FLUORINATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 84872022456     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1318027     Document Type: Article

References (51)

1. Ojima, I., Ed.; Wiley and Sons: New York, 2009.
2. Bégué, J.-P.; Bonnet-Delphon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley and Sons: Hoboken, 2008.
3. Smith, A. M. R.; Hii, K. K. Chem. Rev. 2011, 111, 1637.
4. Valero, G.; Companyó, S.; Rios, R. Chem. Eur. J. 2011, 17, 2018.
5. Lectard, S.; Hamashima, Y.; Sodeoka, M. Adv. Synth. Catal. 2010, 352, 2708.
6. Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917.
7. Cahard, D.; Xu, X.; Couve- Bonnaire, S.; Pannecoucke, X. Chem. Soc. Rev. 2010, 39, 558.
8. Shibatomi, K. Synthesis 2010, 2679.
9. Ueda, M.; Kano, T.; Maruoka, K. Org. Biomol. Chem. 2009, 7, 2005.
10. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1.
11. Brunet, V. A.; O'Hagan, D. Angew. Chem. Int. Ed. 2008, 47, 1179.
12. Shibata, N.; Ishimaru, T.; Nakamura, S.; Toru, T. J. Fluorine Chem. 2007, 128, 469.
13. Hintermann, L.; Togni, A. Angew. Chem. Int. Ed. 2000, 39, 4359.
14. Hamashima, Y.; Yagi, K.; Takano, H.; Tamás, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530.
15. Hamashima, Y.; Takano, H.; Hotta, D.; Sodeoka, M. Org. Lett. 2003, 5, 3225.
16. Shibata, N.; Ishimaru, T.; Nagai, T.; Kohno, J.; Toru, T. Synlett 2004, 1703.
17. Shibata, N.; Kohno, J.; Takai, K.; Ishimaru, T.; Nakamura, S.; Toru, T.; Kanemasa, S. Angew. Chem. Int. Ed. 2005, 44, 4204.
18. Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Tsuchiya, Y.; Moriya, K.; Goto, T.; Sodeoka, M. Tetrahedron 2006, 62, 7168.
19. Shibatomi, K.; Tsuzuki, Y.; Nakata, S.; Iwasa, S. Synlett 2007, 551.
20. Althaus, M.; Becker, C.; Togni, A.; Mezzetti, A. Organometallics 2007, 26, 5902.
21. Shibatomi, K.; Tsuzuki, Y.; Iwasa, S. Chem. Lett. 2008, 37, 1098.
22. Wang, X.; Lan, Q.; Shirakawa, S.; Maruoka, K. Chem. Commun. 2010, 46, 321.
23. Kawatsura, M.; Hayashi, S.; Komatsu, Y.; Hayase, S.; Itoh, T. Chem. Lett. 2010, 39, 466.
24. Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783.
25. Hintermann, L.; Perseghini, M.; Togni, A. Beilstein J. Org. Chem. 2011, 7, 1421.
26. Shibatomi, K.; Narayama, A.; Soga, Y.; Muto, T.; Iwasa, S. Org. Lett. 2011, 13, 2944.
27. Deng, Q.-H.; Wadepohl, H.; Gade, L. H. Chem. Eur. J. 2011, 17, 14922.
28. Bertogg, A.; Hintermann, L.; Huber, D. P.; Perseghini, M.; Sanna, M.; Togni, A. Helv. Chim. Acta 2012, 95, 353.
29. Xu, J.; Hu, Y.; Huang, D.; Wang, K.-H.; Xu, C.; Niu, T. Adv. Synth. Catal. 2012, 354, 515.
30. Suzuki, T.; Goto, T.; Hamashima, Y.; Sodeoka, M. J. Org. Chem. 2007, 72, 246.
31. Reddy, D. S.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. Angew. Chem. Int. Ed. 2008, 47, 164.
32. Bernardi, L.; Jørgensen, K. A. Chem. Commun. 2005, 1324.
33. Hamashima, Y.; Suzuki, T.; Shimura, Y.; Shimizu, T.; Umebayashi, N.; Tamura, T.; Sasamoto, N.; Sodeoka, M. Tetrahedron Lett. 2005, 46, 1447.
34. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309; see also ref. 3f and 3n.
35. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115.
36. Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135.
37. Moriya, K.; Hamashima, Y.; Sodeoka, M. Synlett 2007, 1139.
38. Jacquet, O.; Clément, N. D.; Blanco, C.; Belmonte, M. M.; Benet-Buchholz, J.; van Leeuwen, P. W. N. M. Eur. J. Org. Chem. 2012, 4844.
39. Kwon, B. K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2012, 33, 2481.
40. Hamashima, Y.; Suzuki, T.; Takano, H.; Shimura, Y.; Sodeoka, M. J. Am. Chem. Soc. 2005, 127, 10164.
41. Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem. Int. Ed. 2008, 47, 4157.
42. Zhang, R.; Wang, D.; Xu, Q.; Jiang, J.; Shi, M. Chin. J. Chem. 2012, 30, 1295; see also ref. 3e and 3o.
43. Shibatomi, K.; Muto, T.; Smikawa, Y.; Narayama, A.; Iwasa, S. Synlett 2009, 241.
44. Shibatomi, K.; Soga, Y.; Narayama, A.; Fujisawa, I.; Iwasa, S. J. Am. Chem. Soc. 2012, 134, 9836.
45. Soloshonok, V. A.; Roussel, C.; Kitagawa, O.; Sorochinsky, A. E. Chem. Soc. Rev. 2012, 41, 4180.
46. Nakamura, T.; Tateishi, K.; Tsukagoshi, S.; Hashimoto, S.; Watanabe, S.; Soloshonok, V. A.; Aceña, J. L.; Kitagawa, O. Tetrehedron 2012, 68, 4013.
47. Han, J.; Nelson, D. J.; Sorochinsky, A. E.; Soloshonok, V. A. Curr. Org. Synth. 2011, 8, 310.
48. Ueki, H.; Yasumoto, M.; Soloshonok, V. A. Tetrahedron: Asymmetry 2010, 21, 1396.
49. Soloshonok, V. A.; Ueki, H.; Yasumoto, M.; Mekala, S.; Hirschi, J. S.; Singleton, D. A. J. Am. Chem. Soc. 2007, 129, 12112.
50. Soloshonok, V. A. Angew. Chem. Int. Ed. 2006, 45, 766.
51. Soloshonok, V. A.; Berbasov, D. O. J. Fluorine Chem. 2006, 127, 597.