Enantioselective Fluorination Mediated by Cinchona Alkaloid Derivatives/Selectfluor Combinations:  Reaction Scope and Structural Information for <i>N</i>-Fluorocinchona Alkaloids Norio Shibata Emiko Suzuki Toru Asahi Motoo Shiro 10.1021/ja010789t.s002 https://acs.figshare.com/articles/journal_contribution/Enantioselective_Fluorination_Mediated_by_Cinchona_Alkaloid_Derivatives_Selectfluor_Combinations_Reaction_Scope_and_Structural_Information_for_i_N_i_-Fluorocinchona_Alkaloids/3634461 Cinchona-alkaloid/Selectfluor combinations efficiently fluorinate a variety of carbonyl compounds in a highly enantioselective manner to furnish chiral α-fluorocarbonyl compounds. The DHQB/Selectfluor combination is effective for the enantioselective fluorination of indanones and tetralones <b>1</b> in up to 91% ee. The first enantioselective syntheses of chiral derivatizing reagents <b>3</b> was accomplished with high ee and in high chemical yields by the DHQDA/Selectfluor combination. 3-Fluorooxindoles <b>7</b> were prepared with ee up to 83% using the (DHQ)<sub>2</sub>AQN/Selectfluor or the (DHQD)<sub>2</sub>PYR/Selectfluor combination. Since the combinations are conveniently prepared in situ from readily available reagents, the present system represents a practical method for enantioselective fluorination. X-ray crystallography and <sup>1</sup>H NMR analyses of the cinchona alkaloids/Selectfluor combination have established that the species that mediate this novel reaction are <i>N</i>-fluoroammonium cinchona alkaloid tetrafluoroborates, which adopt open conformations. 2001-06-30 00:00:00 chiral derivatizing reagents 3 DHQDA combination PYR 1 H NMR analyses ee DHQB DHQD Enantioselective Fluorination Mediated fluoroammonium cinchona alkaloid tetrafluoroborates DHQ enantioselective fluorination AQN