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Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters |
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| Authors: | Dr Xu Chen Kaushalendra Patel Prof?Dr Ilan Marek |
| Institution: | 1. Schulich Faculty of Chemistry, Technion – Israel Institute of Technology Technion City, Haifa, 3200009 Israel
These authors contributed equally to this work.;2. Schulich Faculty of Chemistry, Technion – Israel Institute of Technology Technion City, Haifa, 3200009 Israel |
| Abstract: | An efficient method for the stereoselective construction of tertiary C?O bonds via a stereoinvertive nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl carbinol derivatives using water, alcohols and phenols as nucleophiles has been developed. This substitution reaction proceeds under mild conditions and tolerates several functional groups, providing a new access to the stereoselective formation of highly congested tertiary homoallyl alcohols and ethers. |
| Keywords: | Allylic Compounds Cyclopropanes Nucleophilic Substitution Stereoinvertion Synthetic Methods |