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Visible-Light-Mediated Carbonyl Alkylative Amination to All-Alkyl α-Tertiary Amino Acid Derivatives

J. Henry Blackwell, Roopender Kumar and Matthew J. Gaunt*

*Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom, Email:

J. H. Blackwell, R. Kumar, M. J. Gaunt, J. Am. Chem. Soc., 2021, 143, 1598-1609.

DOI: 10.1021/jacs.0c12162

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The use of visible light and a silane reductant enables a carbonyl alkylative amination reaction that combines a wide range of primary amines, α-ketoesters, and alkyl iodides to form functionally diverse all-alkyl α-tertiary amino esters. A Brønsted acid-mediated formation of a ketiminium species is followed by rapid 1,2-addition of an alkyl radical (generated from an alkyl iodide).

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Key Words

amination, alkylation, photochemistry, TTMSS

ID: J48-Y2021