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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
Version:
Accepted Manuscript

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Publisher copy:
10.1021/acs.joc.7b01774

Authors


Brambilla, M More by this author
Brennan, MB More by this author
Csatayová, K More by this author
More by this author
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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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
Pubs id:
pubs:730133
URN:
uri:08c579f6-b082-4cbd-96d2-cfd553c96404
UUID:
uuid:08c579f6-b082-4cbd-96d2-cfd553c96404
Local pid:
pubs:730133
Language:
English

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