Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition–cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids☆
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Add time:09/10/2019 Source:sciencedirect.com
A combination of sulfanyl radical addition–cyclization of the oxime ethers and hydrazones connected with alkenes and subsequent conversion of a phenylsulfanylmethyl group to a carboxyl group provides a novel method for the construction of the cyclic β-amino acids. Upon treatment with thiophenol in the presence of AIBN, the oxime ethers and hydrazones smoothly underwent sulfanyl radical addition-cyclization to give the 2-(phenylsulfanylmethyl)cycloalkylamine. This method was successfully applied to the practical synthesis of 2-aminocyclopentanecarboxylic acid and 4-amino-3-pyrrolidinecarboxylic acid.
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