Journal
ORGANIC LETTERS
Volume 23, Issue 9, Pages 3674-3679Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01062
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Funding
- Department of Science and Technology of Jilin Province [20200801065GH]
- Fundamental Research Funds for the Central Universities [2412020ZD003, 2412020FZ006]
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An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization, with the pendant electron-donating group playing a crucial role in the cyclization process. The strategy has been successfully applied for the first time to construct four-membered heterocycles, as confirmed by both DFT and experimental studies.
An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization of readily available 2-azidoallyl/2-alkoxyallyl alcohols and amines. Notably, this is the first example applying the fluorocyclization strategy to construct four-membered heterocycles. The pendant electron-donating group (-N-3 or -OR) plays a crucial role in polarizing the C=C double bond and facilitating the cyclization process, as verified by DFT and experimental studies.
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