Abstract
AbstractMultifunctional C1‐symmetric organocatalysts were prepared incorporating a camphor‐ and a proline‐based moiety. The new catalysts were evaluated in an asymmetric aldol reaction of acetone and aromatic aldehydes. A significant increase in the catalytic activity was found for the new proline analogue with the camphor‐based 1,3‐diamine unit. This new organocatalyst has one free primary amine group next to the secondary amine group of the proline unit. High yields of up to 97 % with good enantioselectivities (83 % ee) were obtained in the aldol reaction between various aromatic aldehydes and acetone in a shorter reaction time compared with (S)‐proline. A camphor‐based prolineamide analogue with a thiourea group was an efficient multifunctional organocatalyst for the aldol reaction of p‐nitrobenzaldehyde and cyclohexanone with 86 % yield and up to 73 % ee. Moreover, matched‐mismatched studies with opposite stereocenters in the camphor‐based 1,3‐diamine fragment revealed a significant influence of this unit on the overall performance of the new organocatalyst.
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