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Issue 12, 2017
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A practical and scalable system for heteroaryl amino acid synthesis

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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.

Graphical abstract: A practical and scalable system for heteroaryl amino acid synthesis

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Supplementary files

Article information


Submitted
17 Aug 2017
Accepted
02 Oct 2017
First published
02 Oct 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 7998-8003
Article type
Edge Article

A practical and scalable system for heteroaryl amino acid synthesis

R. A. Aycock, D. B. Vogt and N. T. Jui, Chem. Sci., 2017, 8, 7998
DOI: 10.1039/C7SC03612D

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