- 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...
Expand abstract - Publication status:
- Published
- Peer review status:
- Peer reviewed
- Version:
- Publisher's version
- Files:
-
-
(pdf, 1.6mb)
-
- Publisher copy:
- 10.1002/anie.201411924
-
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- 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
- Language:
- English
- Keywords:
- Copyright holder:
- Adam Gammack Yamagata et al.
- Copyright date:
- 2015
- Notes:
- This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Journal article
Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters
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