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Enantioselective silver and amine co-catalyzed desymmetrizing cycloisomerization of alkyne-linked cyclohexanones

Abstract:

A silver(I) and amine co-catalyzed desymmetrization of 4-propargylamino cyclohexanones for the direct enantioselective synthesis of 2-azabicyclo[3.3.1]nonanes is described. Exploiting reactivity arising from dual activation of the pendant terminal alkyne by silver(I) and the ketone moiety through transient enamine formation, this synthetically relevant transformation is easy to perform, efficient and broad in scope. High enantioselectivity (up to 96 % ee) was achieved by exploiting a sign...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted manuscript

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Publisher copy:
10.1002/anie.201612048

Authors


Manzano, R More by this author
More by this author
Institution:
University of Oxford
Oxford college:
St Hilda's College
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
More by this author
Institution:
University of Oxford
Oxford college:
Wadham College
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie International Edition Journal website
Volume:
56
Issue:
21
Pages:
5834-5838
Publication date:
2017-04-21
Acceptance date:
2017-03-28
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Pubs id:
pubs:690768
URN:
uri:fd0ca9c4-b994-4d58-b8c0-cc75515ce2de
UUID:
uuid:fd0ca9c4-b994-4d58-b8c0-cc75515ce2de
Local pid:
pubs:690768

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