Expedient Synthesis and Organocatalytic Studies of Enantiomerically Enriched Benzimidazole-Triazoles
Click chemistry induced synthesis of highly enantiomerically enriched 4-(benzimidazolylmethyl)-1,2,3-triazole derivatives 8(a-g) and 9(a-g) has been achieved. These compounds are bestowed with flexibly bound pi-rich hetero-aryl rings, many binding sites and nucleophilic nitrogens in the vicinity of a chiral center. The synthesis is high yielding and regioselective. The synthesized chiral benzimidazole-triazoles have been found useful as the organocatalyst for the enantioselective Diels-Alder (DA) reaction between anthrone (10) and maleimide detivatives 11(a-g). Enantioselectivity levels were found to be dependent on several factors including nature of substituents in benzimidazole-triazoles 8(a-g) and 9(a-g).
Index Term- Enantiomerically enriched, click chemistry, tweezer, benzimidazole-triazoles, Diels Alder Adduct