期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 72, 期 17, 页码 6459-6463出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo070882l
关键词
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Oxygen-containing heterocyclic systems are important structures in organic chemistry because of their presence in many biologically active compounds. In this work, a Lewis acid-catalyzed cyclization of ethenetricarboxylate derivatives 1 with substituted propargyl alcohols to give methylenetetrahydrofurans was investigated. Reaction of 1 and gamma-silicon-substituted propargyl alcohols 4 with ZnBr2 at 80-110 degrees C led to (Z)-silicon-substituted products stereoselectively. Reaction of 1 and gamma-ester-substituted propargyl alcohol 7 in the presence of various Lewis acids gave ester-substituted methylenetetrahydrofurans stereo selectively. Interesting Lewis acid dependency on stereo selectivity for the reaction of 7 was found. Reaction of a-substituted propargyl alcohols also gave cyclized products.
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