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Synthesis 2008(17): 2825-2829
DOI: 10.1055/s-2008-1067216
DOI: 10.1055/s-2008-1067216
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
Chiral Bifunctional N-Heterocyclic Carbenes: Synthesis and Application in the Aza-Morita-Baylis-Hillman Reaction
Weitere Informationen
Received
21 April 2008
Publikationsdatum:
06. August 2008 (online)
Publikationsverlauf
Publikationsdatum:
06. August 2008 (online)
![](https://www.thieme-connect.de/media/synthesis/200817/lookinside/thumbnails/10.1055-s-2008-1067216-1.jpg)
Abstract
A series of chiral bifunctional N-heterocyclic carbene (NHC) precursors with a proximal hydroxy group were smoothly prepared from l-pyroglutamic acid. Promising enantiomeric excesses (up to 44% ee) were achieved for the bifunctional NHC-catalyzed enantioselective aza-Morita-Baylis-Hillman reaction of cyclopent-2-enone with N-tosylphenylmethanimine.
Key words
N-heterocyclic carbenes - bifunctional catalysts - enantioselective synthesis - aza-Morita-Baylis-Hillman reaction
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