Reeve, P.A.P., Grabowska, U., Oden, L.S. et al. (3 more authors) (2019) Radical functionalization of unsaturated amino acids: synthesis of side-chain-fluorinated, azido-substituted, and hydroxylated amino acids. ACS Omega, 4 (6). pp. 10854-10865. ISSN 2470-1343
Abstract
A range of enantiomerically pure protected side-chain-fluorinated amino acids has been prepared (13 examples) by treatment of protected amino acids containing unsaturated side chains with a combination of Fe(III)/NaBH4 and Selectfluor. The modification of the conditions by replacement of Selectfluor with NaN3 allowed the preparation of side-chain azido-substituted amino acids (five examples), which upon catalytic hydrogenation gave the corresponding amines, isolated as lactams (four examples). Radical hydration of the unsaturated side chains leading to side-chain-hydroxylated protected amino acids has also been demonstrated.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2019 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) (https://creativecommons.org/licenses/by/4.0/) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 26 Jun 2019 14:43 |
Last Modified: | 12 Sep 2019 12:50 |
Status: | Published |
Publisher: | American Chemical Society |
Refereed: | Yes |
Identification Number: | 10.1021/acsomega.9b01509 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:147861 |