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Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

preprint
submitted on 05.04.2020 and posted on 07.04.2020 by Andrey Shatskiy, Anton Axelsson, Björn Blomkvist, Jian-Quan Liu, Peter Dinér, Markus Kärkäs
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.

Funding

KTH Royal Institute of Technology

Olle Engkvists Stiftelse

Wenner-Gren Foundations

Carl Trygger Foundation

History

Email Address of Submitting Author

karkas@kth.se

Institution

KTH Royal Institute of Technology

Country

Sweden

ORCID For Submitting Author

0000-0002-6089-5454

Declaration of Conflict of Interest

The authors declare no competing financial interest

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