Triflic Acid-Catalyzed Cycloisomerization Reactions of Donor–Acceptor Cyclopropanes: Access to Alkyl 5-Arylfuran-2-carboxylates
2016
Zhu, Yuequan | Xu, Panpan | Gong, Yuefa
A direct synthetic strategy starting from alkyl 1-alkoxy-2-aroylcyclopropanecarboxylates was developed for the construction of alkyl 5-arylfuran-2-carboxylates. These donor–acceptor cyclopropanes smoothly undergo a simple ring-opening reaction or/and cycloisomerization reaction in the presence of acid at room temperature, which greatly depends on the properties of the acid used in the experiment. Alkyl 5-arylfuran-2-carboxylates were afforded in high yields in triflic acid, whereas alkyl 2,5-dioxo-5-phenylpentanoate became the major product in other protic acids and Lewis acids.
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