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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

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Publisher copy:
10.1002/anie.201612048

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
St Hilda's College
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Wadham College
Role:
Author
Publisher:
Wiley
Journal:
Angewandte Chemie International Edition More from this journal
Volume:
56
Issue:
21
Pages:
5834-5838
Publication date:
2017-04-21
Acceptance date:
2017-03-28
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
Language:
English
Keywords:
Pubs id:
pubs:690768
UUID:
uuid:fd0ca9c4-b994-4d58-b8c0-cc75515ce2de
Local pid:
pubs:690768
Source identifiers:
690768
Deposit date:
2017-07-02

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