A practical system to synthesize the multiple-substituted 2,5-dihydrofuran by the intermolecular dipolar cycloaddition reactions involving acceptor/acceptor-substituted diazo reagents

作者：Zhu, Shifa^*; Chen, Lijuan; Wang, Chao; Liang, Renxiao; Wang, Xiujun; Ren, Yanwei; Jiang, Huanfeng

来源：Tetrahedron, 2011, 67(30): 5507-5515.

DOI：10.1016/j.tet.2011.05.028

• Diazo
• Dipolar
• Cycloaddition
• 2,5-Dihydrofuran
• Heterocycle

A practical system for synthesizing the multiple-substituted 2,5-dihydrofuran through intermolecular dipolar cycloaddition reactions of acceptor/acceptor diazo reagents, aldehydes, and acetylenedicarboxylate was developed. The reactions proceeded effectively under ambient temperature with low reactant ratios. The control reactions revealed that there are two competitive paths: one forms 1,3-dioxolane and the other forms 2,5-dihydrofuran. These two paths could be controlled by modifying the steric hindrance of the diazo reagents.

• 出版日期2011-7-29
• 单位华南理工大学