Design, synthesis, and application of chiral electron-poor guanidines as hydrogen-bonding catalysts for the Michael reaction

The first chiral electron-poor guanidine organocatalysts were synthesized. The presence of a tunable electron-withdrawing group on the guanidine moiety allows for the modulation of the catalysts’ activity. The application of this new class of organocatalysts to the Michael reaction is demonstrated.

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(E)-N-(((1R,2R)-2-(Dimethylamino)cyclohexylamino)(4-methoxyphenylamino)methylene)-4-methylbenzenesulfonamideC23H32N4O3SEe = 99%[α]D22=-8.2 (c 2.4, CHCl3)Source of chirality: (1R,2R)-(−)-1,2-diaminocyclohexaneAbsolute configuration: (1R,2R)