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Synfacts 2011(2): 0171-0171  
DOI: 10.1055/s-0030-1259267
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Fluoride Generator and Its Application in Kinetic Resolution

Contributor(s): Hisashi Yamamoto, Zhi Li
H. Yan, H. B. Jang, J.-W. Lee, H. K. Kim, S. W. Lee, J. W. Yang, C. E. Song*
Sungkyunkwan University, Suwon, Korea
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

Crown ethers are powerful catalysts to activate anions by coordination with corresponding cations. The authors of this paper introduced an excellent design to add chiral property to such anion activation. Two chiral 3,3′-halo-BINOLs are connected by a partial crown ether linker; therefore, the fluoride anion of KF is activated by multiple coordination between the potassium cation and oxygen atoms as well as iodo groups, because such coordination reduced the electrostatic force between ions.