Article ID Journal Published Year Pages File Type
5216418 Tetrahedron 2014 7 Pages PDF
Abstract

Although thioamides generally undergo a reductive alkylation process when they are treated with a Grignard reagent in the presence of Ti(OiPr)4, substrates fitted with a but-3-enyl substitution at the nitrogen atom are shown to be converted into bicyclic aminocyclopropanes. These reactions are compared with the similar cyclisations of the corresponding carboxylic amide substrates. A mechanistic study is provided. Coincidently, new reagent systems are identified for the mediation of the same transformation.

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Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry