A Facile Stereoselective Synthesis of Internal Conjugated (E,E)-Dienes Including 2,4-Alkadienylamines, -silanes, and stannanes

Article abstract of DOI:10.1021/jo00228a058

Tetrahydropyranyl ethers of 2,4-alkadien-1-ols, prepared by the reaction of 1,3-butadienylmagnesium chloride with carbonyl compounds, are regioselectively attacked on the C-5 position by various lithium reagents, such as RLi, R2NLi, R3SiLi, and R3SnLi, under the elimination of lithium tetrahydropyranyl oxide, giving the corresponding (E,E)-dienes predominantly.