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Synthesis 2011(16): 2540-2548
DOI: 10.1055/s-0030-1260102
DOI: 10.1055/s-0030-1260102
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Synthesis of 2-Substituted Hexahydroquinolin-4-ones Using a Pd-Catalyzed Asymmetric Allylic Amination and Intramolecular Mannich Reaction: Catalytic Asymmetric Synthesis of 2-epi-cis-195A
Weitere Informationen
Received
12 May 2011
Publikationsdatum:
14. Juli 2011 (online)
Publikationsverlauf
Publikationsdatum:
14. Juli 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201116/lookinside/thumbnails/10.1055-s-0030-1260102-1.jpg)
Abstract
A novel method of the enantioselective synthesis of 2-substituted hexahydroquinolin-4-ones is described. The method relies on a Pd-catalyzed asymmetric allylic amination using a chiral diaminophosphine oxide (DIAPHOX) preligand and diastereoselective intramolecular Mannich reaction. The developed synthetic method could be applied to the catalytic asymmetric synthesis of (+)-2-epi-cis-195A.
Key word
asymmetric allylic amination - asymmetric synthesis - chiral diaminophosphine oxide - decahydroquinoline alkaloid - intramolecular Mannich reaction - palladium
- Supporting Information for this article is available online:
- Supporting Information
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References
See Supporting Information for details.
23The enantiomeric excess was determined by chiral HPLC analysis.