An efficient enantioselective fluorination of various β-ketoesters catalyzed by chiral palladium complexes

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14530-14531

  Hamashima, Yoshitaka ^a,b   Yagi, Kenji ^a,b,c   Takano, Hisashi ^a,b   Tamás, László ^a,b   Sodeoka, Mikiko ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c TAKASAGO INTERNATIONAL CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PREDICTION; STEREOCHEMISTRY; TEMPERATURE;

CATALYSIS; ESTERS; HYDROCARBONS, FLUORINATED; KETONES; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 0037065341     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028464f     Document Type: Article

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19. In contrast, no reaction was observed in THF using salt-type fluorine sources such as Selectfluor and N-fluoro-4-methylpyridinium-2-sulfonate.
20. See Supporting Information.
21. In the case of the Michael reaction, no reaction occurred with Pd complex 2. The addition of TfOH, which promoted the reaction as an activator of the enone, was necessary. See ref 9.
22. 2O = 10/1) gave the pure product.
23. Recently, the effects of the stereochemistry of the carbon-fluorine bond on the biological activity of HIV protease inhibitor, indinavir, have been described. See: (a) Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207-7219. In addition, β-amino acids are reported to show a unique protease-resistant character as components of peptidomimetics. The availability of α-fluorinated derivatives will facilitate studies in this field. See: (b) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232. (c) Gademann, K.; Ernst, M.; Hoyer, D.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1223-1226.
24. Recently, the effects of the stereochemistry of the carbon-fluorine bond on the biological activity of HIV protease inhibitor, indinavir, have been described. See: (a) Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207-7219. In addition, β-amino acids are reported to show a unique protease-resistant character as components of peptidomimetics. The availability of α-fluorinated derivatives will facilitate studies in this field. See: (b) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232. (c) Gademann, K.; Ernst, M.; Hoyer, D.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1223-1226.
25. Recently, the effects of the stereochemistry of the carbon-fluorine bond on the biological activity of HIV protease inhibitor, indinavir, have been described. See: (a) Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207-7219. In addition, β-amino acids are reported to show a unique protease-resistant character as components of peptidomimetics. The availability of α-fluorinated derivatives will facilitate studies in this field. See: (b) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232. (c) Gademann, K.; Ernst, M.; Hoyer, D.; Seebach, D. Angew. Chem., Int. Ed. 1999, 38, 1223-1226.
26. The relative configurations of products were tentatively assigned by analogy with the results obtained in the literature. See: Kitazume, T.; Kobayashi, T.; Yamamoto, T.; Yamazaki, T. J. Org. Chem. 1987, 52, 3218-3223.