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. 2009 Jan 10;65(2):449-455.
doi: 10.1016/j.tet.2008.11.027.

Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition

Patrick G McGarraugh  1 , Stacey E Brenner
Affiliations

Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition

Patrick G McGarraugh et al. Tetrahedron. .

Abstract

A new bifunctional organocatalyst with a novel structural and functional motif has been developed. This bifunctional sulfonamide organocatalyst was used in the conjugate addition of 1,3-dicarbonyl compounds (13) to β-nitrostyrenes (12). Yields up to 91% and enantiomeric excesses up to 79% were obtained in this reaction. This catalyst activates both 13 via its basic moiety and 12 through hydrogen bonding.

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Figures

Figure 1
Figure 1
Bifunctional organocatalysts with two H-bond donors
Figure 2
Figure 2
Bissulfonamide organocatalysts with two H-bond donors
Figure 3
Figure 3
Novel bissulfonamide organocatalysts
See this image and copyright information in PMC

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