Lewis Acid-Catalyzed Conjugate Addition-Cyclization Reactions of Ethenetricarboxylates with Substituted Propargyl Alcohols: Stereoselectivity in the Efficient One-Pot Synthesis of Methylenetetrahydrof

详细信息    查看全文

• 作者：Satoshi Morikawa ; Shoko Yamazaki ; Momoko Tsukada ; Suguru Izuhara ; Tsumoru Morimoto ; Kiyomi Kakiuchi
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 17, 2007
• 年：2007
• 卷：72
• 期：17
• 页码：6459 - 6463
• 全文大小：115K
• 年卷期：v.72,no.17(August 17, 2007)
• ISSN：1520-6904

文摘

Oxygen-containing heterocyclic systems are important structures in organic chemistry because of theirpresence in many biologically active compounds. In this work, a Lewis acid-catalyzed cyclization ofethenetricarboxylate derivatives 1 with substituted propargyl alcohols to give methylenetetrahydrofuranswas investigated. Reaction of 1 and -silicon-substituted propargyl alcohols 4 with ZnBr₂ at 80-110 Cled to (Z)-silicon-substituted products stereoselectively. Reaction of 1 and -ester-substituted propargylalcohol 7 in the presence of various Lewis acids gave ester-substituted methylenetetrahydrofuransstereoselectively. Interesting Lewis acid dependency on stereoselectivity for the reaction of 7 was found.Reaction of -substituted propargyl alcohols also gave cyclized products.