Synthesis of Highly Substituted Unsymmetrical 1,2-Diamines, 1,2-Diimines, Imidazolium Salts and Imidazolylidenes by Aldimine Cross-Coupling

α-Aminonitriles derived from aromatic aldehydes and primary amines can be deprotonated quantitatively without the use of protecting groups. The 1,2-addition of the resulting stabilized α-aminocarbanions to imines yields α-aminoimines and the tautomeric enediamines. These unstable compounds can directly be oxidized to 1,2-diimines or reduced to 1,2-diamines in a one-pot reaction. 1,2-Diamines can be obtained in high diastereoselectivity by reduction of the 1,2-diimines. In this case, the relative configuration of the products can be chosen depending on the reduction conditions. Cyclization of the unsymmetrical diimines with halomethyl ethers or esters leads to 1,3,4,5-tetrasubstituted imidaz…

Modular synthesis of tetrasubstituted imidazoles and trisubstituted oxazoles by aldimine cross-coupling.

An Aldimine Cross-Coupling for the Diastereoselective Synthesis of Unsymmetrical 1,2-Diamines

ChemInform Abstract: Modular Synthesis of Tetrasubstituted Imidazoles and Trisubstituted Oxazoles by Aldimine Cross-Coupling.

One-Pot Synthesis of Trisubstituted 1,2-Amino Alcohols from Deprotonated α-Amino Nitriles

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. This procedure leads to the predominant formation of the anti-configured products. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Eine gekreuzte Aldiminkupplung zur diastereoselektiven Synthese von unsymmetrischen 1,2-Diaminen

CCDC 601965: Experimental Crystal Structure Determination

Related Article: Coralie Kison, Till Opatz|2006|Synthesis||3727|doi:10.1055/s-2006-950237