Journal article icon

Journal article

Hydrogen‐bond‐enabled dynamic kinetic resolution of axially chiral amides mediated by a chiral counterion

Abstract:

Non‐biaryl atropisomers are valuable in medicine, materials, and catalysis, but their enantioselective synthesis remains a challenge. Herein, a counterion‐mediated O‐alkylation method for the generation of atropisomeric amides with an er up to 99:1 is outlined. This dynamic kinetic resolution is enabled by the observation that the rate of racemization of atropisomeric naphthamides is significantly increased by the presence of an intramolecular O−H⋅⋅⋅NCO hydrogen bond. Upon O‐alkylation of the...

Expand abstract
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's Version

Actions


Access Document


Files:
Publisher copy:
10.1002/anie.201814362

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
Role:
Author
Expand authors...
Publisher:
John Wiley and Sons, Ltd. Publisher's website
Journal:
Angewandte Chemie International Edition Journal website
Volume:
58
Issue:
9
Pages:
2795-2798
Publication date:
2019-02-06
Acceptance date:
2019-01-08
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Pubs id:
pubs:959943
URN:
uri:8f409272-989c-4202-af37-35a346a30af5
UUID:
uuid:8f409272-989c-4202-af37-35a346a30af5
Local pid:
pubs:959943

Terms of use


Metrics


Views and Downloads






If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP