A Novel Stereoselective or Stereospecific Alkylation of α, β or β, γ-Unsaturated Esters

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Abstract
The alkylation of α, β-unsaturated esters with n-butylbromide gave stereoselectively α-butyl-β, γ-cis-unsaturated esters in the presence of alkali amide in liquid ammonia. On the other hand, the alkylation of β, γ-cis or trans-unsaturated esters afforded α-butyl-β, γ- cis or trans-unsaturated esters with retention of configuration. These alkylations provide a new synthetic method of preparing α-alkyl β, γ-cis or trans-unsaturated esters.

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