ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES. AN EFFICIENT SYNTHESIS OF (R)- AND (S)-3,4-EPOXY-1-BUTANOL

Article abstract of DOI:10.1016/S0040-4020(01)86092-0

The synthesis of enantiomerically pure 5-menthyloxy-2(5H)-furanones is described as well as the diastereoselective 1,4-addition of thiols to these butenolides to yield new homochiral C4-synthons.Kinetic resolution of 5-methoxy-2(5H)-furanone, with an enantiomeric excess of 13percent, was achieved by cinchonidine catalysed thiophenol addition. The synthetic utility of the asymmetric thiol additions is illustrated in an efficient route to enantiomerically pure (R)- and (S)-3,4-epoxy-1-butanol.