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A mild and efficient aza-Diels-Alder reaction of N-benzhydryl imines with trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene catalyzed by Yb(OTf)3
Authors:Ke Cheng
Institution:Key Laboratory of Green Chemistry and Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
Abstract:The aza-Diels-Alder reaction of trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene with N-benzhydryl imines in the presence of Yb(OTf)3 in toluene at room temperature gave the corresponding 2,5-disubstituted 2,3-dihydro-4-pyridones in high yields. This reaction can also be carried out with diene, aldehydes, and amine in a three-component one-pot reaction manner in moderate to high yields under solvent-free conditions. The relationship between Lewis acids and activity, solvents and catalyst loading were studied. Some investigation towards the reaction mechanism was discussed.
Keywords:Nitrogen heterocycles  Cycloaddition  N-Benzhydryl imines  Ytterbium
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