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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
Version:
Publisher's version

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Publisher copy:
10.1002/anie.201411924

Authors


Gammack Yamagata, AD More by this author
Jackson, KE More by this author
Stegbauer, L More by this author
More by this author
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
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European Commission More from this funder
Funded Access More from this funder
Publisher:
Wiley Online Library Publisher's website
Journal:
Angewandte Chemie Journal website
Volume:
54
Issue:
16
Pages:
4899–4903
Publication date:
2015-04-07
DOI:
ISSN:
1433-7851 and 1521-3773
Pubs id:
pubs:509932
URN:
uri:6aca3459-892a-48ea-ab86-d2128a6f112b
UUID:
uuid:6aca3459-892a-48ea-ab86-d2128a6f112b
Local pid:
pubs:509932

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