Journal article

Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids

Abstract:: For the first time we have been able to employ enantiopure 1,2‐amino alcohols derived from abundant amino acids in C‐C bond forming hydrogen borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub‐stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ‐aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen borrowing intermediate, removing the need for column chromatography.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Hall, C. J. J., Goundry, W., & Donohoe, T. (2021). Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids. Angewandte Chemie International Edition, 60(13), 6981–6985.

MLA Style

Hall, CJJ, et al. “Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids.” Angewandte Chemie International Edition, vol. 60, no. 13, 2021, pp. 6981–85.

Chicago Style

Hall, CJJ, W Goundry, and T Donohoe. 2021. “Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids.” Angewandte Chemie International Edition 60 (13): 6981–85.
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Files:: Hall_et_al_2021_Hydrogen_Borrowing_Alkylation.pdf

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Publisher copy:: 10.1002/anie.202100922

Authors

+ Hall, CJJ More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Role:: Author

+ Goundry, W More by this author

Role:: Author

+ Donohoe, T More by this author

Institution:: University of Oxford
Department:: CHEMISTRY
Sub department:: Organic Chemistry
Role:: Author

Publisher:: Wiley
Journal:: Angewandte Chemie International Edition More from this journal
Volume:: 60
Issue:: 13
Pages:: 6981-6985
Publication date:: 2021-02-24
Acceptance date:: 2021-02-09
DOI:: 10.1002/anie.202100922
EISSN:: 1521-3773
ISSN:: 1433-7851

Language:: English
Keywords:: FFR
Pubs id:: 1160477
Local pid:: pubs:1160477
Deposit date:: 2021-02-09
ARK identifier:: ark:/29072/ora_6b2b80b03aee461b9c5dfa85008c961f

Terms of use

Copyright holder:: Wiley
Copyright date:: 2021
Rights statement:: © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

Licence:: CC Attribution (CC BY)

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