ChemInform Abstract: Lewis Acid Catalyzed α-Functionalization of Ketals for the Regioselective Synthesis of α-Carbamoyl Ketals.
Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-1167, USA.Organic Letters (Impact Factor: 6.36). 07/2012; 14(15):3952-4. DOI: 10.1021/ol301710w
Treatment of 1 with DEAD in the presence of BF(3)·OEt(2) gave 2 (R = H), which was N-alkylated to give 2 (R = CH(2)CO(2)Et), and insitu eliminated (E1cb) to give α-carbamoyl ketals.
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ABSTRACT: An efficient Cu-catalyzed C–H amination of 2-alkylazaarenes with azodicarboxylates has been developed through nucleophilic addition of sp3C–H bond to unsaturated nitrogen–nitrogen double bond. It provides an easy access to azaarene-containing hydrazines from simple and easily available starting materials.Tetrahedron Letters 02/2013; 54(7):711–714. DOI:10.1016/j.tetlet.2012.12.055 · 2.38 Impact Factor
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