Abstract
A novel class of tetrahetero-substituted 1,3-dienes 1a−d having aryl ether substituents at the 1,3-positions were synthesized by enol silylation of 4-substituted 1,3-diphenoxy-3-buten-2-ones 3a−c. The 1Z,3Z configuration of 1b has been assigned by X-ray crystallography. The synthesis of triaryl ethers utilizing a Diels−Alder approach involved reaction of diene 1a with methyl acrylate to furnish a 3:1 mixture of endo- and exo-adducts. Conversion of the adducts to cyclohexenone 8 and aromatization with DDQ gave triaryl ether 9. Cycloaddition reactions of 1a, 1b with some conjugated alkenes exhibited excellent regiospecificity and endo stereoselectivity.
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