高价碘介导的丙烯酰胺-氨基甲酸酯的氧化环化反应生成 5,5-二取代恶唑烷-2,4-二酮。
Hypervalent Iodine Mediated Oxidative Cyclization of Acrylamide -Carbamates to 5,5-Disubstituted Oxazolidine-2,4-diones.
机构信息
Department of Pharmacological and Pharmaceutical Sciences, College of Pharmacy, University of Houston, Health Building 2, Room 7036, Houston, Texas 77204-5000, United States.
Department of BioMolecular Sciences, Division of Medicinal Chemistry, School of Pharmacy, University of Mississippi, University, Mississippi 38677-1848, United States.
出版信息
J Org Chem. 2020 Jun 5;85(11):7549-7557. doi: 10.1021/acs.joc.0c00581. Epub 2020 May 11.
A metal-free oxidative cyclization of -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 with -Boc-2,3-dimethylacrylamides and proceeded with phenyl migration in the case of an -Boc-2-phenylacrylamide to generate a 5-acetoxy-5-benzyloxazolidine-2,4-dione.
在乙酸中，用（二乙酰氧基碘）苯对 Boc-丙烯酰胺进行无金属氧化环化反应，以中等至优秀的收率生成 5,5-二取代恶唑烷-2,4-二酮，同时形成 C-O 键。此外，-Boc-2,3-二甲基丙烯酰胺的反应具有立体选择性，而在 -Boc-2-苯丙烯酰胺的情况下，反应伴随着苯基迁移，生成 5-乙氧基-5-苯甲氧基恶唑烷-2,4-二酮。
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