| Abstract
| - A novel class of tetrahetero-substituted 1,3-dienes1a−d having aryl ether substituents at the1,3-positions were synthesized by enol silylation of 4-substituted1,3-diphenoxy-3-buten-2-ones 3a−c.The 1Z,3Z configuration of 1b hasbeen assigned by X-ray crystallography. The synthesis oftriarylethers utilizing a Diels−Alder approach involved reaction of diene1a with methyl acrylate to furnisha 3:1 mixture of endo- and exo-adducts. Conversion of the adductsto cyclohexenone 8 andaromatization with DDQ gave triaryl ether 9.Cycloaddition reactions of 1a, 1b withsomeconjugated alkenes exhibited excellent regiospecificity and endostereoselectivity.
|
