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A long-standing challenge within radical chemistry is that of controlling the absolute stereochemistry of the products. Here, we report the stereocontrolled addition of α-amino radicals reductively generated from imines via… Click to show full abstract
A long-standing challenge within radical chemistry is that of controlling the absolute stereochemistry of the products. Here, we report the stereocontrolled addition of α-amino radicals reductively generated from imines via visible-light-mediated photoredox-catalysis to alkenes, giving rise to enantioenriched α-trialkyl-α-tertiary amines. This process exploits a commercially available phenylglycinol derivative as a source of both nitrogen and chiral information. DFT studies support a stereochemical model whereby an intramolecular H-bond rigidifies the transition state of the enantiodetermining step.
Journal Title: Organic Letters
Year Published: 2023
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