CATALYTIC KINETIC RESOLUTION OF 5-ALKOXY-2(5H)-FURANONES

The kinetic resolution of racemic 5-alkoxy-2(5H)-furanones, using a ch iral aminoalcohol catalyzed 1-4-addition of arylthiols, was examined. Using various butenolides it was shown that a gamma-alkoxy substituent appears to be essential to reach high enantioselectivities whereas el ectron-donating substituents in the arylthiols also increase the selec tivity. Cinchona alkaloids are the preferred catalysts for the kinetic resolution, with quinine and quinidine leading to the most efficient and selective thiol additions. A remarkable dilution effect and a stro ng dependency on the mode of addition of reactants were observed. Opti mization studies are presented of the kinetic resolution of 5-methoxy- 2(5H)-furanone 2 resulting in (R)-2 or (S)-2 with enantiomeric excesse s exceeding 90%. A mechanism for the quinine (quinidine) catalyzed kin etic resolution is given.