No protecting groups are required for the cross‐coupling of N‐monosubstituted α‐aminonitriles with imines. Depending on the workup procedure, highly substituted unsymmetrical 1,2‐diamines or 1,2‐diimines can be prepared in a one‐pot procedure. The diastereoselective reduction of the diimines furnishes either the syn‐ or the anti‐configurated diamines (see scheme).

From five to two: The addition of deprotonated Strecker products to N‐acylimines permits the synthesis of tetrasubstituted imidazoles or trisubstituted oxazoles in three or four steps, respectively. In total, the target compounds are prepared from two aldehydes, a primary amine, an acid chloride and ammonia (see scheme).

Ohne Schutzgruppen gelingt die Kreuzkupplung von N‐monosubstituierten α‐Aminonitrilen mit Iminen. Je nach Aufarbeitung der Reaktionsmischung können so im Eintopfverfahren unsymmetrische hochsubstituierte 1,2‐Diamine oder 1,2‐Diimine erhalten werden. Durch diastereoselektive Reduktion der Diimine sind wahlweise die syn‐ oder die anti‐konfigurierten Diamine zugänglich (siehe Schema).

A short synthesis of N,1,2-trisubstituted vicinal amino alcohols by 1,2-addition of deprotonated N-monosubstituted α-amino nitriles to aldehydes and subsequent one-pot reduction of the intermediates with borane-THF is described.

Amines Q 0120An Aldimine Cross-Coupling for the Diastereoselective Synthesis of Unsymmetrical 1,2-Diamines. -A new flexible method is presented. The formation of syn-or anti-configurated products depends on the choice of work-up and reduction conditions. -(KISON, C.; MEYER, N.; OPATZ*, T.; Angew. Chem., Int. Ed. 44 (2005) 35, 5662-5664; Inst. Org. Chem., Johannes-Gutenberg-Univ.,