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Synfacts 2006(1): 0075-0075  
DOI: 10.1055/s-2005-921710
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Thiourea Derivative Catalyzed Asymmetric Aza-Baylis-Hillman Reaction

Contributor(s): Benjamin List, Michael Stadler
I. T. Raheem, E. N. Jacobsen*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
16 December 2005 (online)

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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.