Inhaltszusammenfassung

alpha-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 alpha-aminocarbanions to imines yields alpha-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 cas...alpha-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 alpha-aminocarbanions to imines yields alpha-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.» weiterlesen» einklappen

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DDC Sachgruppe:
Chemie