Diene-transmissive Diels-Alder Cycloaddition Reaction of Bis(silyloxy) Cross-conjugated Trienes

Abstract

Abstract Multiple Diels-Alder reaction of bis(silyloxy) cross-conjugated trienes is presented. Two trienes, 3-benzylidene- and 3-(methoxymethylene)-2,4-bis(trimethylsilyloxy)-1,4-pentadiene, undergo two sequential Diels-Alder cycloadditions with a variety of dienophiles forming hydronaphthalene rings. Some characteristics of this reaction have been discussed in terms of stereo-, regio-, and chemoselectivity. It is proposed that this process is referred to as “diene-transmissive Diels-Alder reaction”.