Per-6-amino-β-cyclodextrin catalyzed asymmetric Michael addition of nitromethane and thiols to chalcones in water

An environmentally benign and enantioselective Michael addition of nitromethane/thiols to trans-chalcone catalyzed by per-6-amino-β-cyclodextrin (per-6-ABCD) is carried out in water at room temperature with good yield and enantiomeric excess. The catalyst is recovered and reused without loss in its activity.

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(S)-4-Nitro-1,3-diphenylbutan-1-oneEe = 68.5% (by Chiral HPLC with chiralcel AD-H column)[α]D25=-11.1 (c 1.00, CH2Cl2)Source of chirality: per-6-amino-β-cyclodextrinAbsolute configuration: (3S)