Organocatalytic Cloke-Wilson Rearrangement: Carbocation-Initiated Tandem Ring Opening/Cyclization of Cyclopropanes under Neutral Conditions

Guisheng Zhang*, Liming Chen, Zhaokang Hu, Zhiguo Zhang*, Jingjing Bi, Mengjuan Li and Xingjie Zhang

*School of Chemistry and Chemical Engineering, Henan Normal University, 46 East of Construction Road, Xinxiang, Henan 453007, China, Email: zgshtu.edu.cn, zhangzghtu.edu.cn

G. Zhang, L. Chen, Z. Hu, Z. Zhang, J. Bi, M. Li, X. Zhang, J. Org. Chem., 2023, 88, 1003-1017.

DOI: 10.1021/acs.joc.2c02415

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Abstract

2-(Bromomethyl)naphthalene promotes an organocatalytic and base-free Cloke-Wilson rearrangement of chain doubly activated cyclopropanes for the construction of 2,3-dihydrofurans via a carbocation-initiated tandem intramolecular ring-opening/recyclization process. The strategy is especially suitable for the construction of furan units in complex molecules.

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proposed mechanism

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Key Words

2,3-dihydrofurans, organocatalysis

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ID: J42-Y2023