Sheppard, TD;
Sabatini, M;
Karaluka, V;
Lanigan, RM;
Boulton, LT;
Badland, M;
(2018)
Protecting‐Group‐Free Amidation of Amino Acids using Lewis Acid Catalysts.
Chemistry - A European Journal
10.1002/chem.201800372.
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Abstract
Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.
| Type: | Article |
|---|---|
| Title: | Protecting‐Group‐Free Amidation of Amino Acids using Lewis Acid Catalysts |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/chem.201800372 |
| Publisher version: | https://doi.org/10.1002/chem.201800372 |
| Language: | English |
| Additional information: | This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ |
| Keywords: | Amides, amino acids, boron, catalysis, green chemistry |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Population Health Sciences > UCL GOS Institute of Child Health UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10047995 |
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