期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 353, 期 14-15, 页码 2721-2730出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100282
关键词
alkaloids; aza-Michael addition; iminium catalysis; organocatalysis; piperidines
资金
- 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
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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