Electrostatic Repulsion and Hydrogen‐Bonding Interactions in a Simple <i>N</i>‐Aryl‐<scp>L</scp>‐valinamide Organocatalyst Control the Stereoselectivity in Asymmetric Aldol Reactions

Abstract

Abstract A novel stereocontrol method for asymmetric aldol reactions of aldehydes with ketones is described. The stereoselectivity of the products is controlled by the electrostatic repulsion and hydrogen‐bonding interactions of an N ‐aryl‐ L ‐valinamide catalyst. The use of this catalyst in a cross‐aldol reaction allows easy access to bioactive 3‐cyclohexanone‐3‐hydroxy‐2‐oxindole with excellent diastereo‐ ( syn / anti = &gt;99:1) and enantioselectivity (&gt;99 % ee ).