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Journal article

Probing competitive and co-operative hydroxyl and ammonium hydrogen-bonding directed epoxidations

Abstract:

The diastereoselectivities and rates of epoxidation (upon treatment with Cl3CCO2H then m-CPBA) of a range of cis- and trans-4-aminocycloalk-2-en-1-ol derivatives (containing five-, six-, and seven-membered rings) have been investigated. In all cases where the two potential directing groups can promote epoxidation on opposite faces of the ring scaffold, evidence of competitive epoxidation pathways, promoted by hydrogen-bonding to either the in situ formed ammonium moiety or the hydroxyl group,...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.joc.7b01774

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Publisher:
American Chemical Society Publisher's website
Journal:
Journal of Organic Chemistry Journal website
Volume:
82
Issue:
19
Pages:
10297–10309
Publication date:
2017-08-31
Acceptance date:
2017-08-31
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Pmid:
28858526
Source identifiers:
730133
Language:
English
Pubs id:
pubs:730133
UUID:
uuid:08c579f6-b082-4cbd-96d2-cfd553c96404
Local pid:
pubs:730133
Deposit date:
2017-09-22

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