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Synfacts 2006(1): 0075-0075
DOI: 10.1055/s-2005-921710
DOI: 10.1055/s-2005-921710
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York
Thiourea Derivative Catalyzed Asymmetric Aza-Baylis-Hillman Reaction
I. T. Raheem, E. N. Jacobsen*
Harvard University, Cambridge, USA
Further Information
Publication History
Publication Date:
16 December 2005 (online)
![](https://www.thieme-connect.de/media/synfacts/200601/lookinside/thumbnails/10.1055-s-2005-921710-1.jpg)
Significance
The asymmetric aza-Baylis-Hillman reaction of N-p-nitrobenzenesulfonylimines with methyl acrylate, mediated by chiral thiourea derivatives and one equivalent of DABCO as nucleophile, is described. While the coupling of methyl acrylate with a variety of aromatic amines furnishes the products in good to excellent enantioselectivities (87-99% ee), yields are moderate (25-49%). Viable imine substrates are electron-donating, electron-withdrawing and heteroaromatic compounds.