Lewis acid promoted reactions of ethenetricarboxylates with allenes: synthesis of indenes and γ-lactones via conjugate addition/cyclization reaction

S Yamazaki, Y Yamamoto, Y Fukushima…

Index: Yamazaki, Shoko; Yamamoto, Yuko; Fukushima, Yugo; Takebayashi, Masachika; Ukai, Tetsuma; Mikata, Yuji Journal of Organic Chemistry, 2010 , vol. 75, # 15 p. 5216 - 5222

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Citation Number: 20

Abstract

Indenes are important core structures in organic chemistry. Few simple arylallenes have been used to construct indene skeletons by Friedel− Crafts reaction. Lewis acid catalyzed reaction of ethenetricarboxylates 1 and arylallenes has been examined in this study. The reaction of arylallenes and ethenetricarboxylate triesters with SnCl4 gave indene derivatives efficiently, via a conjugate addition/Friedel− Crafts cyclization reaction. On the other hand, ...