Organocatalysed Asymmetric β‐Amination and Multicomponent syn ‐Selective Diamination of α,β‐Unsaturated Aldehydes

An easy and affordable route for obtaining chiral β‐aminated‐ and α,β‐diaminated aldehydes, 1,3‐aminoalcohols, and related compounds by using organocatalysis is presented. The chiral secondary amine ( S )‐2‐[bis(3,5‐bistrifluoromethylphenyl)trimethylsilanyloxymethyl]pyrrolidine is used as the catalyst to activate α,β‐unsaturated aldehydes, which allows succinimide to add in a 1,4‐regio‐ and stereoselective fashion thereby forming N‐protected 1,3‐aminoaldehydes in good yields and enantioselectivities. This is followed by two easy transformations giving rise to optically active 1,3‐aminoalcohols, a common motif in many biologically active compounds, for example, fibrinogen receptor antagonists. Furthermore, optically active α,β‐ syn ‐diaminated aldehydes were obtained by the addition of diethyl azodicarboxylate in a one‐pot reaction.