Volume 225, 2021

Face-selective adsorption of a prochiral compound on the chiral pore-surface of a metal–macrocycle framework (MMF) directed towards stereoselective reactions

Abstract

Molecular adsorption on a surface is a unique way to break the mirror-symmetry of prochiral molecules, and therefore the use of chiral surfaces is an effective strategy for achieving highly selective chiral separation and asymmetric catalytic reactions based on molecular adsorption with high diastereoselectivity. We have previously reported a porous metal–macrocycle framework (MMF) with an enantiomeric pair of chiral pore-surfaces derived from PdII3-helical macrocycles as the ingredients of the framework. Aiming at applying the chiral pore-surface of the MMF to asymmetric reactions and chiral separation, herein we propose a strategy to utilize one of the enantiomerically paired pore-surfaces as a homochiral pore-surface with the aid of chiral auxiliaries that can block only one side of the enantiomeric pore-surfaces in a site-selective manner. Single-crystal X-ray diffraction analysis revealed that a chiral auxiliary, (1R)- or (1S)-1-(3-chlorophenyl)ethanol, and a prochiral guest molecule, 2′-hydroxyacetophenone, were cooperatively arranged in each pore unit so that the prochiral guest molecule can face-selectively bind to the homochiral pore-surface.

Graphical abstract: Face-selective adsorption of a prochiral compound on the chiral pore-surface of a metal–macrocycle framework (MMF) directed towards stereoselective reactions

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
03 фев 2020
Accepted
09 апр 2020
First published
09 апр 2020

Faraday Discuss., 2021,225, 197-209

Face-selective adsorption of a prochiral compound on the chiral pore-surface of a metal–macrocycle framework (MMF) directed towards stereoselective reactions

S. Tashiro, T. Umeki, R. Kubota and M. Shionoya, Faraday Discuss., 2021, 225, 197 DOI: 10.1039/D0FD00019A

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