Lewis Acid-Initiated Ring-Opening Reactions of Five- and Six-Membered Cyclic Ethers Based on the Oxonium Ylide Intermediates
Dandan Jiang,
Jun Xiao,
Yingzhen Zhang,
Kunming Liu,
Juanhua Li,
Jinbiao Liu
Affiliations
Dandan Jiang
Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China
Jun Xiao
Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China
Yingzhen Zhang
Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China
Kunming Liu
Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China
Juanhua Li
Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China
Jinbiao Liu
Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China
In light of the small ring strain of five/six-membered cyclic ethers, constructing complex molecules via ring-opening reactions has consistently been a highly challenging topic in organic synthesis. Induced by Lewis acids, the charge redistribution in cyclic ethers forms oxonium ylide intermediates, thereby activating the C–O bond and subsequently facilitating nucleophilic attack for ring opening. In recent years, a variety of novel Lewis acids, encompassing those with new metal centers and frustrated Lewis pairs (FLPs), have been effectively utilized to induce the formation of oxonium ylides, offering a diverse array of methods for the ring opening of five/six-membered cyclic ethers. This review conveys the extensive application advancements of diverse Lewis acid types for cyclic ether ring-opening reactions over the past two decades, originating from the perspective of the classification of Lewis acids. Furthermore, the substrate applicability and chemical transformation efficiency of these Lewis acids in the ring-opening reactions of cyclic ethers have also been discussed herein.
