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ORGANIC LETTERS
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c04308
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We report the stereocontrolled addition of alpha-amino radicals to alkenes through visible-light-mediated photo-redox-catalysis, generating enantioenriched alpha-trialkyl-alpha- tertiary amines. This process utilizes a commercially available phenylglycinol derivative as a source of nitrogen and chiral information. DFT studies confirm the role of an intramolecular H-bond in rigidifying the transition state of the enantiodetermining step.
A long-standing challenge within radical chemistry is that of controlling the absolute stereochemistry of the products. Here, we report the stereocontrolled addition of alpha-amino radicals reductively generated from imines via visible-light-mediated photo-redox-catalysis to alkenes, giving rise to enantioenriched alpha-trialkyl-alpha- 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.
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