Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 14-15, Pages 2721-2730Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100282
Keywords
alkaloids; aza-Michael addition; iminium catalysis; organocatalysis; piperidines
Categories
Funding
- NSFC [20802030, 21072082, 20921120404]
- MOST [2010CB833200]
- Chinese Ministry of Education [109154]
- Fok Ying Tung Education Foundation [121015]
- NCET [NCET-08-0254]
- Fundamental Research Funds for the Central Universities [lzujbky-2010-k09]
- Lanzhou University
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The synthetically useful functionalized 2-substituted piperidines containing a lateral ketone group have been strategically accessed via an organocatalytic enantioselective intramolecular aza-Michael addition of enone carbamates, in which a novel internal substrate combination of the enone moiety as Michael acceptor and the carbamate moiety as Michael donor was revealed in asymmetric bifunctional organocatalysis. This heteroatom conjugate addition, which was realized by using a catalytic chiral Cinchona-based primary-tertiary diamine and an achiral Bronsted acid, mostly proceeded in high yield and good to excellent stereocontrol (up to 99% ee). This reaction provides an alternative catalytic asymmetric method for installing the stereogenic nitrogen-containing carbon center in functionalized 2-substituted piperidines, leading to the development of a straightforward and expeditious synthesis of some naturally occurring bioactive 2-substituted piperidine alkaloids.
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