Preparation and Reactivity of Acyclic Chiral Allylzinc Species by a Zinc‐Brook Rearrangement |
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| Authors: | Dr Markus Leibeling Dr Khriesto A Shurrush Dr Veronika Werner Dr Lionel Perrin Prof Ilan Marek |
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| Institution: | 1. The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa, Israel;2. ICBMS UMR 5246, Université de Lyon, Bat. Curien, Villeurbanne Cedex 5, France |
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| Abstract: | The zinc‐Brook rearrangement of enantiomerically enriched α‐hydroxy allylsilane produces a chiral allylzinc intermediate, which reacts with retention of configuration in the presence of an electrophile. Two remarkable features of this transformation are the stereochemical outcome during the formation of the allylzinc species and the complete stereocontrol in the organized six‐membered transition state, which leads to an overall and complete transfer of chirality within the reaction sequence. |
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| Keywords: | allylic compounds Brook rearrangement chirality olefins zinc |
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