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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 cl...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1002/anie.202100922

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Role:
Author
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:
EISSN:
1521-3773
ISSN:
1433-7851
Language:
English
Keywords:
Pubs id:
1160477
Local pid:
pubs:1160477
Deposit date:
2021-02-09

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