Enantiodivergent Aldol Condensation in the Presence of Aziridine/Acid/Water Systems
Adam Marek Pieczonka,
Lena Marciniak,
Michał Rachwalski,
Stanisław Leśniak
Affiliations
Adam Marek Pieczonka
Department of Organic and Applied Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland
Lena Marciniak
The Bio-Med-Chem Doctoral School of the University of Lodz and Lodz Institutes of the Polish Academy of Sciences, University of Lodz, 91-403 Lodz, Poland
Michał Rachwalski
Department of Organic and Applied Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland
Stanisław Leśniak
Department of Organic and Applied Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland
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).
