A Facile Method for the Stereoselective Preparation of (1Z, 3E)-Dienyl Ethers via 1,4-Elimination of 1,4-Dialkoxy-(2Z)-alkenes with n-Butyllithium

Treatment of 1-alkoxy-4-methoxy-(2Z)-alkenes or 1-sil-oxy-4-methoxy-(2Z)-alkenes with n-butyllithium in diethyl ether is shown to afford the corresponding (1Z,3E)-dienyl, alkyl or silyl ethers, respectively, in high stereoselectivity via a facile 1,4-elimination. The scope and the regio- and stereochemical features of the synthetic method are described