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Lewis Acid Promoted Reactions of Ethenetricarboxylates with Allenes: Synthesis of Indenes and gamma-Lactones via Conjugate Addition/Cyclization Reaction

  作者 YAMAZAKI SHOKO; YAMAMOTO YUKO; FUKUSHIMA YUGO; TAKEBAYASHI MASACHIKA; UKAI TETSUMA; MIKATA YUJI  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-15;  页码  5216-5222  
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[摘要]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, the reactions of 1,1-diethyl 2-hydrogen ethenetricarboxylate and arylallenes or alkylallenes with SnCl4 at -78 degrees C or room temperature and subsequent treatment with Et3N gave gamma-lactones. The reactions of triethyl ethenetricarboxylate and 1,1-dialkylallenes with SnCl4 at room temperature also gave gamma-lactones.

 
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