Stereoselective synthesis of unnatural α-amino acid derivatives through photoredox catalysis

Andrey Shatskiy; Anton Axelsson; Elena V. Stepanova; Jian-Quan Liu; Azamat Z. Temerdashev; Bhushan P. Kore; Björn Blomkvist; James M. Gardner; Peter Dinér; Markus D. Kärkäs

doi:10.1039/D1SC00658D

Stereoselective synthesis of unnatural α-amino acid derivatives through photoredox catalysis†

Andrey Shatskiy,

^a Anton Axelsson,^a Elena V. Stepanova,

^bc Jian-Quan Liu,

^a Azamat Z. Temerdashev,

^d Bhushan P. Kore,^e Björn Blomkvist,^a James M. Gardner,

^e Peter Dinér

^a and Markus D. Kärkäs

*^a

Author affiliations

* Corresponding authors

^a Division of Organic Chemistry, Department of Chemistry, KTH Royal Institute of Technology, SE-100 44, Stockholm, Sweden
E-mail: karkas@kth.se

^b Tomsk Polytechnic University, Lenin Avenue 30, 634050 Tomsk, Russia

^c Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia

^d Department of Analytical Chemistry, Kuban State University, Stavropolskaya St. 149, 350040 Krasnodar, Russia

^e Division of Applied Physical Chemistry, Department of Chemistry, KTH Royal Institute of Technology, SE-100 44, Stockholm, Sweden

Abstract

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived N-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. Alternative mechanisms for the developed transformation are discussed and corroborated by experimental and computational studies.

Chemical Science

Stereoselective synthesis of unnatural α-amino acid derivatives through photoredox catalysis†

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Stereoselective synthesis of unnatural α-amino acid derivatives through photoredox catalysis

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