Rapid Access to 2-Methylene Tetrahydrofurans and γ-Lactones: A Tandem Four-Step Process

Angewandte Chemie
Renxiao LiangShifa Zhu

Abstract

A one-pot tandem process involving hydrolysis, Knoevenagel condensation, Michael addition, and Conia-ene (HKMC) reactions has been developed for the rapid synthesis of indanone-fused 2-methylene tetrahydrofurans from the reaction of enynals and propynols. In this process, two rings and four bonds are generated with 100 % atom-economy and high step-efficiency. The resulting tetrahydrofurans were readily oxidized into α-methylene γ-lactones, which are one of the most important substructures in natural and bioactive compounds.

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Citations

Jan 18, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Guillaume CompainElisabet Duñach
Feb 16, 2017·Chemical Communications : Chem Comm·Changyuan ZhangShifa Zhu
Mar 6, 2018·Chemistry : a European Journal·Jiantao ZhangShifa Zhu
Oct 28, 2016·Chemical Communications : Chem Comm·Yuefeng ZhouShifa Zhu
Nov 8, 2018·Organic & Biomolecular Chemistry·Lianfen ChenShifa Zhu
Mar 19, 2019·Chemistry : a European Journal·Jiantao ZhangShifa Zhu
Dec 14, 2018·Organic Letters·Bishnupada SatpathiS S V Ramasastry
May 24, 2019·The Journal of Organic Chemistry·Ni-Ni ZhouHai-Tao Zhu

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