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Copper-Catalyzed Intramolecular Hydroalkoxylation of α-(1-Hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-Endo Mode for Preparation of 2-Alkyl- and 2-Aryl-2,5-dihydrofurans

Sanghyuck Kim and Phil Ho Lee*

*Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea, Email: phleekangwon.ac.kr

S. Kim, P. H. Lee, J. Org. Chem., 2012, 77, 215-220.

DOI: 10.1021/jo2018125 (free Supporting Information)


Abstract

Ethyl α-(1-hydroxy-1-alkyl)methylallenoates and α-(1-hydroxy-1-aryl)methylallenoates undergo an efficient and selective copper-catalyzed intramolecular hydroalkoxylation to give functionalized 3-ethoxycarbonyl-2-alkyl- and -aryl-2,5-dihydrofurans in good to excellent yields through a 5-endo mode.


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Synthesis of 2-Alkyl- and Aryl-3-ethoxycarbonyl-2,5-dihydrofurans through Gold-Catalyzed Intramolecular Hydroalkoxylation

D. Eom, D. Kang, P. H. Lee, J. Org. Chem., 2010, 75, 7447-7450.


Key Words

2,5-dihydrofurans


ID: J42-Y2012-0020