Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

07 April 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. The mechanism for the developed transformation is discussed and the stereodetermining radical addition step was studied by the DFT calculations.


amino acids
carboxylic acids
photoredox catalysis
stereoselective synthesis

Supplementary materials

Sulfinimine SI - 20200405


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