Journal
ORGANIC LETTERS
Volume 22, Issue 5, Pages 2105-2110Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00619
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Funding
- Japan Society for the Promotion of Science (JSPS) [JP16H06354, JP16K05680]
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An efficient method for the synthesis of tetrasubstituted furans was developed by utilizing the [1,2]-phospha-Brook rearrangement under Bronsted base catalysis. The two-step one -pot formal [3 + 2] cycloaddition involves the nucleophilic addition of a propargyl anion, which is catalytically generated through the [1,2]-phospha-Brook rearrangement, to an aldehyde and the subsequent intramolecular cyclization mediated by N-iodosuccinimide to provide 2,4,5-trisubstituted-3-iodofurans. The present method with readily available substrates provides new access to a wide range of well -organized tetrasubstituted furans.
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