Diene-transmissive Hetero Diels-Alder Reaction of 1,5-Diphenyl-1,4-pentadien-3-one

Abstract

Ahstmct -The diene-transmissive hetero Diels-Alder reaction of 1,s-diphenyl-1.4pentadien-%one is described.Stereoselectivity of the inverse electron-demand Diels-Alder reaction of electron-rich vinyl ethers at the first stage was greately affected by the nature of Lewis acid-catalysts: The ZnX2 (X=CI, I)-, MgBr2-and E ~( f o d ) ~catalyzzd reactions gave the corresponding endo-adducts, whereas exo-adducts were formed in the GaBr3-, AICL-, and Et2A1CI-catalyzed reactions.In the sequential Diels-Alder reaction initial cycloadducts readily reacted with electron-deficient dienophiles such as 1,2,4-triazolinedions, tetracyanoethene, and maleimides to give the corresponding cross-his-cycloadducts.The diene-transmissive Diels-Alder reaction of cross-conjugated trienes122 and heterotrienes3-' offers a versatile synthetic route to hydronaphthalene-and heteroatom-containing hydronaphthalene-skeletons.