Synthesis of novel enantiomerically pure tetra-carbohydrazide cyclophane macrocycles?

Organic & Biomolecular Chemistry Pub Date: 2012-04-03 DOI: 10.1039/C2OB25171J

Abstract

A total of twelve novel enantiomerically pure tetra-carbohydrazide cyclophane macrocycles have been synthesised in quantitative yields by reacting chiral (4R,5R)- and (4S,5S)-1,3-dioxolane-4,5-dicarbohydrazides with aromatic bis-aldehydes in a [2?+?2]-cyclocondensation reaction. The compounds show a dynamic behaviour in solution, which has been rationalized in terms of an unprecedented conformational interconversion between two conformers one stabilised by intramolecular hydrogen bonding and π–π stacking interactions.

Graphical abstract: Synthesis of novel enantiomerically pure tetra-carbohydrazide cyclophane macrocycles
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