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The catalytic activity of racemic thiourea derivatives of Troger’s base (±)-2–4 in Michael additions of malonate derivatives to trans-β-nitrostyrene was studied. Due to the low basicity of Troger’s base, the outcome of the addition reactions was strongly dependent on the pKa of the nucleophile. Thiourea catalysts (±)-2, 3 were resolved on the chiral stationary phase Whelk O1. Unfortunately, enantiopure catalysts 2 and 3 showed no stereoselectivity in the Michael addition.

Thiourea derivatives of Tröger’s base: synthesis, enantioseparation and evaluation in organocatalysis of Michael addition to nitroolefins