Zincke's Reaction with Chiral Primary Amines: A Practical Entry to Pyridinium Salts of Interest in Asymmetric Synthesis

Yves Genisson; Christian Marazano; Maryam Mehmandoust; Dino Gnecco; Bhupesh C. Das

doi:10.1055/s-1992-21371

Synlett 1992; 1992(5): 431-434
DOI: 10.1055/s-1992-21371

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Zincke's Reaction with Chiral Primary Amines: A Practical Entry to Pyridinium Salts of Interest in Asymmetric Synthesis

Yves Genisson^* , Christian Marazano, Maryam Mehmandoust, Dino Gnecco, Bhupesh C. Das

^*Institut de Chimie des Substances Naturelles, CNRS, F-91128 Gif-sur-Yvette Cedex, France

Abstract

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The scope of Zincke's synthesis of pyridinium salts using various chiral primary amines and mono- or dialkylpyridines substituted at positions 3, 4 or 5 has been investigated. Salts 6a-f, 9a-i, and 10b,e,h-j were obtained in excellent yields. The results support the accepted mechanism for Zincke's reaction and shows the influence of the solvent on the course of this reaction.

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