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Overcoming Regioselectivity Issues Inherent in Bis-Tröger's Base Preparation

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journal contribution
posted on 12.10.2006, 00:00 by Martin Havlík, Vladimír Král, Bohumil Dolenský
Bis-Tröger's base derivatives are a new family of molecular tweezers. A major drawback to their study is a lack of commercially available precursors, ortho-nitrocarboxylic acids. A reverse synthetic strategy starting from known dinitrodicarboxylic acids, which circumvents this problem, is presented. Via this methodology regioisomeric bis-TB derivatives can be prepared selectively, using only common aromatic amines that are typically commercially available.