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Updated: Jun 11, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various
Yutaro Miyashita1, Sae Someya1, Tomoko Kawasaki-Takasuka1
1Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan.
Abstract:
We describe herein a facile method to access 2,3-epoxyesters with fluorine-containing substituents at their 3-position starting from the corresponding enoates by utilization of the low-costed and easy-to-handle reagent, NaOCl·5H2O. Because very little has been disclosed about the reactivity of such 2,3-epoxyesters, their epoxy ring opening by a variety of nucleophiles was carried out and we succeeded in clarifying these chemo- as well as regioselective processes proceeding via the SN2 mechanism to mainly afford 2-substituted 3-hydroxyesters usually in a highly anti selective manner.
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