Hydromagnesiation of 1-Arylallenes with Magnesium Hydride toward Cinnamylmagnesium Reagents
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Updated: Apr 18, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Jaslyn Jing Wen Ng1,2, Eugene Yew Kun Tan1, Yihang Li1
1School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore.
Abstract:
We herein report that magnesium hydride, generated via solvothermal treatment of magnesium iodide with sodium hydride in tetrahydrofuran, is capable of promoting the hydromagnesiation of 1-arylallenes. The resulting cinnamylmagnesium species could be functionalized by the subsequent treatment with aldehydes or ketones in the presence of zinc chloride to form various homoallylic alcohols in a diastereoselective manner via a 6-membered ring chair-like transition state.
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