Abstract
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 imidazolium
salts which can serve as starting materials for the preparation of highly substituted
nucleophilic carbenes.
Key words
cross-coupling - carbenes - 1,2-diamines - nitrogen heterocycles - reduction
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