97719-35-2Relevant academic research and scientific papers
ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES. AN EFFICIENT SYNTHESIS OF (R)- AND (S)-3,4-EPOXY-1-BUTANOL
Feringa, Ben L.,Lange, Ben De
, p. 7213 - 7222 (2007/10/02)
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.
ASYMMETRIC MICHAEL ADDITION OF THIOPHENOL TO MALEIC ACID ESTERS
Yamashita, Hiroyuki,Mukaiyama, Teruaki
, p. 363 - 366 (2007/10/02)
(S)-(-)-Diisopropyl phenylthiosuccinate (81percent optical purity) is prepared in 95percent yield by the asymmetric Michael addition of thiophenol to diisopropyl maleate in the presence of a catalytic amount of cinchonine.The succinate thus prepared is transformed into (R)-(+)-3,4-epoxy-1-butanol without racemization.
