A practical and scalable system for heteroaryl amino acid synthesis

• Type of Material: Article
• Authors: R. A. Aycock, Emory University School of Medicine; D. B. Vogt, Emory University School of Medicine; Nathan T. Jui, Emory University
• Language: English
• Date: 2017-01-01
• Publisher: Royal Society of Chemistry: Open Access
• Publication Version: Final Published Version
• Copyright Statement: © 2017 The Royal Society of Chemistry.
• License: Creative Commons Attribution 3.0 Unported
• Final Published Version (URL): http://dx.doi.org/10.1039/c7sc03612d
• Title of Journal or Parent Work: Chemical Science
• ISSN: 2041-6520
• Volume: 8
• Issue: 12
• Start Page: 7998
• End Page: 8003
• Grant/Funding Information: Financial support was provided by Emory University and Winship Cancer Institute.
• Research Categories: Health Sciences, Oncology; Chemistry, General

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.