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

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...

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Veröffentlicht in:Journal of organic chemistry 2007-01, Vol.72 (1), p.246-250
Hauptverfasser: Suzuki, Toshiaki, Goto, Tomomi, Hamashima, Yoshitaka, Sodeoka, Mikiko
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Sprache:eng
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Zusammenfassung: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).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo062048m