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Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters

Abstract:

A new catalytic asymmetric desymmetrization reaction for the synthesis of enantioenriched derivatives of 2-azabicyclo[3.3.1]nonane, a key motif common to many alkaloids, has been developed. Employing a cyclohexanediamine-derived primary amine organocatalyst, a range of prochiral cyclohexanone derivatives possessing an α,β-unsaturated ester moiety linked to the 4-position afforded the bicyclic products, which possess three stereogenic centers, as single diastereoisomers in high enantioselectiv...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1002/anie.201411924

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Publisher:
Wiley Publisher's website
Journal:
Angewandte Chemie Journal website
Volume:
54
Issue:
16
Pages:
4899–4903
Publication date:
2015-04-07
DOI:
ISSN:
1521-3773 and 1433-7851
Pmid:
25727215
Language:
English
Keywords:
Pubs id:
pubs:509932
UUID:
uuid:6aca3459-892a-48ea-ab86-d2128a6f112b
Local pid:
pubs:509932
Deposit date:
2016-09-06

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