Homochiral Self-Sorting of BINOL Macrocycles?

Chemical Science Pub Date: 2013-09-02 DOI: 10.1039/C3SC52018H

Abstract

Chiral arylene–ethynylene macrocycles (AEMs) were synthesized via alkyne metathesis-mediated depolymerization of BINOL-based polymers. Homochiral dimers are selectively obtained from metathesis of heterochiral polymers. Thermodynamic analysis and computational modeling suggests the homochiral self-sorting to be entropy-driven due to the greater symmetry of the homochiral dimers over the heterochiral dimer. This symmetry-controlled reaction is a novel approach to achieving high selectivity in dynamic covalent macrocycle synthesis. Importantly, the result describes a new paradigm in dynamic covalent chemistry that will enable efficient synthesis of new chiral architectures.

Graphical abstract: Homochiral Self-Sorting of BINOL Macrocycles
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