High-fidelity stereochemical memory in a Fe(II)4L4 tetrahedral capsule.

J Am Chem Soc

Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom.

Published: November 2013

A new class of Fe(II)4L4 capsules, based upon a tritopic trialdehyde subcomponent, is reported. One such capsule was prepared diastereoselectively through the incorporation of a chiral amine residue. This amine was displaced by an achiral one, while maintaining the stereochemistry of the cage framework (99% ee); this cage retained its stereochemistry even after 4 days at 90 °C. Mechanistic studies indicate the memory displayed by this capsule to be the result of effective stereochemical communication between the metal centers mediated by the rigid 3-fold-symmetric faces, in combination with a stepwise substitution mechanism.

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http://dx.doi.org/10.1021/ja410117qDOI Listing

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