Abstract
Abstract The stereoselectivity of diene-transmissive Diels–Alder reaction of a cross-conjugated triene, 3-benzylidene-2,4-bis(trimethylsilyloxy)-1,4-pentadiene, with a variety of olefinic dienophiles was investigated. Cyclic dienophiles gave the stereoselective bis-adducts via the endo mono-cycloadducts, whereas the exo mono-adducts were obtained as major products in the reaction with acyclic dienophiles. The steric regulation of diene-transmissive Diels–Alder reaction was discussed.
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