Synthesis of functionalized and fused furans and pyrans from the Morita-Baylis-Hillman acetates of nitroalkenes

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• 作者：Divya K. Nair ; Shaikh M. Mobin ; Irishi N.N. Namboothiri ; ^{irishi@iitb.ac.in}
• 关键词：Furan ; Pyran ; Nitroalkene ; Morita&ndash ; Baylis&ndash ; Hillman acetates ; Cascade reaction
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：27 June, 2012
• 卷：53
• 期：26
• 页码：3349-3352
• 文件大小：1069 K

摘要

The Morita-Baylis-Hillman (MBH) acetates derived from nitroalkenes and ethyl glyoxylate have been transformed in one pot at room temperature to highly fused and functionalized furans and pyrans in good to excellent yield. The reaction involves a cascade Michael-oxa-Michael addition of 尾-dicarbonyl compounds to the MBH acetates in the presence of an amine base such as DABCO. An unusual switching of selectivity in the oxa-Michael addition from 5-exo-trig to 6-endo-trig was observed when the 尾-dicarbonyl compound was changed from acyclic or six-membered ring cyclic to five-membered ring cyclic system.