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Synthesis of a bicyclic oxo-γ-lactam from a simple caprolactam derivative

Abstract:
The synthesis of the 6-azabicyclo[3.2.1]octane ring system, via Dieckmann cyclization, is described. Ring closure involves reaction of a caprolactam enolate with a C-6 ester, the reactive axial conformation of which is promoted by the presence of an N-tert-butyloxycarbonyl group on the lactam nitrogen. The results will enable the synthesis of new bridged caprolactams for testing as antibacterials and nucleophilic enzyme inhibitors.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/C7NJ02348K

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
ORCID:
0000-0002-0290-6565
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Role:
Author
ORCID:
0000-0001-5056-8778
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Name:
Medical Research Council
Funding agency for:
Schofield, C
More from this funder
Name:
University of Freiberg
Funding agency for:
Gruber, T
Weck, C
Publisher:
Royal Society of Chemistry
Journal:
New Journal of Chemistry More from this journal
Volume:
41
Issue:
18
Pages:
9984-9989
Publication date:
2017-08-04
Acceptance date:
2017-07-27
DOI:
EISSN:
1369-9261
ISSN:
1144-0546
Pubs id:
pubs:730968
UUID:
uuid:09dc078e-06be-46c9-8f88-4cc320772414
Local pid:
pubs:730968
Source identifiers:
730968
Deposit date:
2018-04-12

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