Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins |
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| Authors: | Xuan Zhou Haye Min Ko Guangbin Dong |
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| Institution: | 1. Department of Chemistry, University of Texas at Austin, Austin, Texas, USA;2. Department of Chemistry, University of Chicago, Chicago, Illinois, USA;3. Department of Bio-Nano Chemistry, Wonkwang University, Jeonbuk, Republic of Korea |
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| Abstract: | Herein, we report an intramolecular rhodium‐catalyzed decarbonylative coupling between cyclobutanones and alkenes that proceeds by C?C activation and provides a distinct approach to a diverse range of saturated bridged cyclopentane derivatives. In this reaction, cyclobutanones serve as cyclopropane surrogates, reacting in a formal (4+2?1) transformation. To demonstrate the efficacy of this method, it was applied in a concise synthesis of the antifungal drug Tolciclate. |
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| Keywords: | C− C activation cycloaddition cyclobutanones decarbonylation rhodium catalysis |
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