Ruffling-induced chirality: Synthesis, metalation, and optical resolution of highly nonplanar, cyclic, benzimidazole-based ligands

T Fekner, J Gallucci, MK Chan

Index: Fekner, Tomasz; Gallucci, Judith; Chan, Michael K. Journal of the American Chemical Society, 2004 , vol. 126, # 1 p. 223 - 236

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Citation Number: 57

Abstract

Expedient five-step syntheses of a cyclic bis (benzimidazole)-based amide 5 and two sterically more hindered analogues 23-24 have been developed. These amides are chiral due to the inherent ruffling of the macrocyclic plane. Racemization of the optical antipodes of these compounds has been studied using dynamic chiral stationary phase HPLC. These studies reveal that, while the parent amide 5 racemizes rapidly, for the sterically more ...