Synlett

FeCl3-Catalyzed Propargylation-Cycloisomerization Tandem Reaction: A Facile One-Pot Synthesis of Substituted Furans

W Ji, Y Pan, S Zhao, Z Zhan

Index: Ji, Wen-Hua; Pan, Ying-Ming; Zhao, Su-Yan; Zhan, Zhuang-Ping Synlett, 2008 , # 19 p. 3046 - 3052

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Citation Number: 26

Abstract

Reaction of propargylic alcohol 1a (1: X = OH; R ¹ = Ph; R ² = TMS) with ethyl acetoacetate (3a; R ³ = Me; R 4 = OEt) under the reaction conditions (5 mol% FeCl 3 , toluene, rt), produced the coupling product 4a (R ¹ = Ph; R ² = TMS; R ³ = Me; R 4 = OEt) in low yield, and no cycloisomerization product 5aa (R ¹ = Ph; R ² = H; R ³ = Me; R 4 = OEt) was obtained. Gratifyingly, the tandem propargylic substitution-cycloisomerization proceeded well at reflux temperature for 0.8 hour, ...

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