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A Redox-Relay Heck Approach to Substituted Tetrahydrofurans

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An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available cis-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that… Click to show full abstract

An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available cis-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that can be directly reduced to afford the corresponding 3-aryl tetrahydrofuran. Furthermore, the hemiacetals can also serve as precursors to a range of disubstituted tetrahydrofurans, including the calyxolane natural products.

Keywords: redox relay; heck approach; substituted tetrahydrofurans; relay heck

Journal Title: Organic Letters
Year Published: 2023

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