Current Search: Hintze, Silas Q. (x)
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Title
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Base Promoted 5-endo-dig Cyclizations of Non-Conia-ene Propargyl Ethers: A Mechanistic Investigation.
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Creator
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Hintze, Silas Q., Lepore, Salvatore D., Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
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Abstract/Description
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Herein, we discuss a novel method for the synthesis of decorated 2,5-dihydrofurans. The base promoted 5-endo-dig cyclization of non-Conia-ene propargyl ethers produces 2,2 disubstituted dihydrofurans. Central to the reaction is the presence of an acidic C–H bond which is activated by an adjacent aromatic heterocycle. The transformation is viable with a wide range of substituents, including N, O, and S containing heterocycles, substituted phenyl rings, and alkyl groups. The cyclization...
Show moreHerein, we discuss a novel method for the synthesis of decorated 2,5-dihydrofurans. The base promoted 5-endo-dig cyclization of non-Conia-ene propargyl ethers produces 2,2 disubstituted dihydrofurans. Central to the reaction is the presence of an acidic C–H bond which is activated by an adjacent aromatic heterocycle. The transformation is viable with a wide range of substituents, including N, O, and S containing heterocycles, substituted phenyl rings, and alkyl groups. The cyclization proceeds within 30 seconds at room temperature under the action of potassium tert-butoxide. This work stands apart from the current literature due to the absence of transition metal catalysts and/or harsh reaction conditions. A thorough mechanistic investigation is undertaken to better understand the nature of this unprecedented reaction.
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Date Issued
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2024
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PURL
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http://purl.flvc.org/fau/fd/FA00014376
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Subject Headings
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Cyclization (Chemistry), Chemistry, Organic
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Format
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Document (PDF)
