(ALLYLTHIO)ACETATE DIANION AS A MEW AND CONVENIENT REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF (2E,4E)DIENOATES FROM ALKYL HALIDES

Article abstract of DOI:10.1246/cl.1981.315

Treatment of (allylthio)acetate with lithium diisopropylamide followed by the addition of s-butyllithium produced a new dianion which could react with a variety of alkyl halides exclusively at the allylic position.The high regioselectivity of the allylic alkylation could be realized in the case of methyl (allylthio)acetate dianion.A convenient and general method for the stereoselective synthesis of (2E,4E)dienoates from alkyl halides has been developed.