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In the process of improving the synthesis of a novel class of chiral drug scaffolds, first reported in 2010, we observed that the stereochemical outcome of the key chemical transformation appeared to be correlated to the solvophobicity of the reaction medium. Our mechanistic investigations by NMR monitoring of the reaction confirmed the proposed acylation/intermolecular cycloaddition sequence. The...
In the past, bicyclic structures mimicking dipeptides have been designed and successfully used to prepare enzyme inhibitors. We report herein our preliminary results in the design and expedient synthesis of a novel series of diastereomeric N-amino-hexahydro-1H-isoindolone scaffolds built from three commercially available building blocks in only two steps, with high yields, a single protecting group...
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