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. 2017 Dec 1;8(12):7998-8003.
doi: 10.1039/c7sc03612d. Epub 2017 Oct 2.

A practical and scalable system for heteroaryl amino acid synthesis

R A Aycock  1 , D B Vogt  1 , N T Jui  1
Affiliations

A practical and scalable system for heteroaryl amino acid synthesis

R A Aycock et al. Chem Sci. .

Abstract

A robust system for the preparation of β-heteroaryl α-amino acid derivatives has been developed using photoredox catalysis. This system operates via regiospecific activation of halogenated pyridines (or other heterocycles) and conjugate addition to dehydroalanine derivatives to deliver a wide range of unnatural amino acids. This process was conducted with good efficiency on large scale, the application of these conditions to amino ketone synthesis is shown, and a simple protocol is given for the preparation of enantioenriched amino acid synthesis, from a number of radical precursors.

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Figures

Fig. 1
Fig. 1. Impact of pyridine incorporation into amino acids and peptide drugs.
Fig. 2
Fig. 2. A proposed mechanism of heteroaryl radical conjugate addition to dehydroalanine.
See this image and copyright information in PMC

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