Synthesis of 4-hydroxy-and 2, 4-dihydroxy-homophthalates by [4+ 2] cycloaddition of 1, 3-bis (silyloxy)-1, 3-butadienes with dimethyl allene-1, 3-dicarboxylate

…, M Sher, A Mahal, A Villinger, C Fischer, P Langer

Index: Hussain, Ibrar; Yawer, Mirza A.; Appel, Bettina; Sher, Muhammad; Mahal, Ahmed; Villinger, Alexander; Fischer, Christine; Langer, Peter Tetrahedron, 2008 , vol. 64, # 34 p. 8003 - 8009

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Citation Number: 14

Abstract

Allenes represent versatile synthetic building blocks in inter- and intramolecular [4+2] cycloadditions. 1 The [4+2] cycloaddition of 2-silyloxy-1,3-dienes with allenes has been reported to give functionalized phenols. For example, (R)-(+)-lasiodiplodin was prepared based on the cyclization of a cyclic allenylester with 1,1-dimethoxy-3-trimethylsilyloxy-1,3-butadiene. 2 The reaction of allenylphenylsulfone with Danishefsky's diene afforded 3-methyl-4-( ...