Reduction of ethyl 2-alkyl- and 2,3-dialkyl-2-cyclopropene-1-carboxylates and the corresponding cyclopropenols with lithium aluminum hydride

Abstract

1. The reduction of ethyl 2,3-dialkylcyclopropane-1-carboxylates either take place with retention of the double bond in the ring or leads to the corresponding alcohols of the cyclopropane series, depending on the reaction conditions. 2. Complete reduction takes place stereospecifically; in the products the hydroxymethyl group is in the trans position in relation to the alkyl substituants. 3. The regioselectivity of the reduction process (the direction of initial attack by the hydride ion) is determined by the possibility of the formation of the most stable carbanion.