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Asymmetric nucleophilic fluorination under hydrogen bonding phase-transfer catalysis

Abstract:

Common anionic nucleophiles such as those derived from inorganic salts have not been used for enantioselective catalysis because of their insolubility. Here, we report that merging hydrogen bonding and phase-transfer catalysis provides an effective mode of activation for nucleophiles that are insoluble in organic solvents. This catalytic manifold relies on hydrogen bonding complexation to render nucleophiles soluble and reactive, while simultaneously inducing asymmetry in the ensuing transfor...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1126/science.aar7941

Authors


More by this author
Institution:
University of Oxford
Department:
Chemistry; Organic Chemistry
Role:
Author
ORCID:
0000-0003-3084-3888
More by this author
Institution:
University of Oxford
Department:
Chemistry; Organic Chemistry
Role:
Author
ORCID:
0000-0002-2739-4156
More by this author
Institution:
University of Oxford
Department:
Chemistry; Organic Chemistry
Role:
Author
ORCID:
0000-0003-2083-8735
More by this author
Institution:
University of Oxford
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Chemistry; Organic Chemistry
Role:
Author
More from this funder
Name:
Engineering and Physical Sciences Research Council
Grant:
EP/L015838/1
More from this funder
Name:
European Commission
Grant:
316882
More from this funder
Name:
Lilly Research Award Program
Publisher:
American Association for the Advancement of Science
Journal:
Science More from this journal
Volume:
360
Issue:
6389
Pages:
638-642
Publication date:
2018-05-11
Acceptance date:
2018-03-21
DOI:
EISSN:
1095-9203
ISSN:
0036-8075
Pmid:
29748281
Language:
English
Pubs id:
pubs:847412
UUID:
uuid:90f7ccc6-12ab-4a3b-ba1a-98965b5fd999
Local pid:
pubs:847412
Source identifiers:
847412
Deposit date:
2018-06-08

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