Unexpected Beneficial Effect of ortho-Substituents on the (S)-Proline-Catalyzed Asymmetric Aldol Reaction of Acetone with Aromatic Aldehydes

Martínez A., van Gemmeren M., List B.

Abstract

An intriguing effect of electronegative 2,6-substituents on the stereochemical outcome of (S)-proline-catalyzed aldol reactions between benzaldehyde derivatives and acetone is reported. Remarkably high enantioselectivities can be achieved with such substrates. © Georg Thieme Verlag Stuttgart New York.