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Versatility in the Brook Rearrangement for the Selective Ring-Opening of Three-Membered Rings
Authors:Dr. Coralie Tugny  Dr. Fa-Guang Zhang  Prof. Dr. Ilan Marek
Affiliation:The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Technion City, 3200009 Haifa, Israel
Abstract:From a single α-silylated carbinol intermediate, easily accessible by carbometallation of cyclopropenes, various scaffolds featuring a quaternary carbon stereocenter could be obtained selectively. The selectivity towards these different products was achieved by either changing the experimental conditions or the nature of the organometallic species involved.
Keywords:Brook rearrangement  cyclopropane  fragmentation  quaternary carbon  selectivity
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