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Updated: Jul 19, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols
Yannick Linne1, Daniel Lohrberg1, Henry Struwe1
1Institute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, 30167 Hannover, Germany.
Abstract:
The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki-Hiyama-Takai-Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe-Matteson-Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy.
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