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Enantioselective Fluorination of tert-Butoxycarbonyl Lactones and Lactams Catalyzed by Chiral Pd(II)-Bisphosphine Complexes

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journal contribution
posted on 05.01.2007 by Toshiaki Suzuki, Tomomi Goto, Yoshitaka Hamashima, Mikiko Sodeoka
An efficient catalytic enantioselective fluorination of tert-butoxycarbonyl lactones and lactams is reported. Reactions of the lactone substrates proceeded smoothly in an alcoholic solvent with a catalytic amount of chiral Pd(II) complex. In the case of the less acidic lactam substrates, concurrent use of the Pd complex and 2,6-lutidine as a cocatalyst was effective. Under the reaction conditions, the fluorinated lactones and lactams were obtained in good yield with excellent enantioselectivity (94−99% ee).