Enantiodivergent Aldol Condensation in the Presence of Aziridine/Acid/Water Systems

Abstract

A series of novel chiral imines was synthesized from corresponding aldehydes and 1-(2-aminoalkyl)aziridines with good chemical yields. Such imines were tested as catalysts in the direct asymmetric aldol reaction between aromatic aldehydes and acetone/cyclohexanone in the presence of catalytic amounts of water and an acidic additive. The corresponding aldol products were formed in excellent yields and with very high enantioselectivities (98% and 99% ee, respectively).

Keywords

• asymmetric synthesis
• enantiodivergent aldol condensation
• diastereodivergent process
• aziridines
• chiral imines
• enantioselectivity