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Communication | Special issue | Vol 50, No. 2, 1999, pp.661-666
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)91
■ Diene-transmissive Hetero Diels-Alder Reaction of 1,5-Diphenyl-1,4-pentadien-3-one

Otohiko Tsuge,* Taizo Hatta, Toshitsugu Fujiwara, Tomoya Yokohari, Akihiko Tsuge, and Tetsuji Moriguchi

*Department of Applied Chemistry, Sojo University, 4-22-1, Ikeda, Kumamoto-shi, 860-0082, Japan

Abstract

The diene-transmissive hetero Diels-Alder reaction of 1,5-diphenyl-1,4-pentadien-3-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=Cl, I)-, MgBr2- and Eu(fod)3-catalyzed reaction gave the corresponding endo-adducts, whereas exo-adducts were formed in the GaBr3-, AlCl3-, and Et2AlCl-catalyzed reactions. In the sequential Diels-Alder reaction initial cycloadducts readily reacted with electron-deficient dienophile such as 1,2,4-triazolinedions, tetracyanoethene, and maleimides to give the corresponding cross-bis-cycloadducts.