Hypervalent Iodine Mediated Oxidative Cyclization of Acrylamide N -Carbamates to 5,5-Disubstituted Oxazolidine-2,4-diones
Hypervalent Iodine Mediated Oxidative Cyclization of Acrylamide N -Carbamates to 5,5-Disubstituted Oxazolidine-2,4-diones
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高价碘介导丙烯酰胺 N-氨基甲酸酯氧化环化为 5,5-二取代恶唑烷-2,4-二酮
DOI：
10.1021/acs.joc.0c00581
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Cuny, Gregory D.
中科院分区：
文献类型：
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作者：
Duddupudi, Anantha Lakshmi;Pandey, Pankaj;Vo, Hien;Welsh, Colin L.;Doerksen, Robert J.;Cuny, Gregory D.
N-叔丁氧羰基丙烯酰胺与二乙酰氧基碘代苯在乙酸中无金属氧化环化生成5，5-二取代恶唑烷-2，4-二酮，并形成C-O键，产率中等至优异。此外，该反应与N-Boc-2，3-二甲基丙烯酰胺是非对映特异性的，并且在N-Boc-2-苯基丙烯酰胺的情况下进行苯基迁移以生成5-乙酰氧基-5-苄基恶唑烷-2，4-二酮。
A metal-free oxidative cyclization ofN-Boc-acrylamides with (diacetoxyiodo)benzene in acetic acid produced 5,5-disubstituted oxazolidine-2,4-diones with the formation of a C–O bond in moderate to excellent yields. In addition, the reaction was diastereospecific withN-Boc-2,3-dimethylacrylamides and proceeded with phenyl migration in the case of anN-Boc-2-phenylacrylamide to generate a 5-acetoxy-5-benzyloxazolidine-2,4-dione.