Chirality in Organic Hosts

Fankhauser, Daniel; Easton, Christopher J.

doi:10.1002/9781118867334.ch11

Cited by 1 publication

(1 citation statement)

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“…Therefore, development of novel chiral receptors or supramolecular frameworks provides tools for the stereochemical understanding of complex biological systems. For example, chiral cyclodextrins (CDs) have been used as artificial hosts mimicking various enzyme activities, and chiral corands have been utilized as transacylase mimics . Similarly, chiral porphyrins have been designed to model oxygen uptake and oxygen transport processes, and chiral crown-ethers have been employed to mimic natural ion channels …”

Section: Introductionmentioning

confidence: 99%

Inherently Chiral Bambus[4]urils

Mohite

Reany

2020

J. Org. Chem.

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A new class of bambus [4]urils (BU[4]s) composed of asymmetric N,N′-disubstituted glycoluril subunits with different alkyl groups were designed, synthesized, and fully characterized by NMR techniques and X-ray crystallography. Structural studies showed that four macrocyclic diastereoisomers are possible: two S n symmetric achiral macrocycles and two macrocycles that are "inherently" chiral. The relative "head-to-tail" arrangement of the N-substituents in Bn 4 Me 4 BU[4], 5a, clearly observed by X-ray spectroscopy analysis, determines the overall symmetry of the bambusuril structure. Chiral Pr 4 Me 4 BU[4], 4b, was resolved by chiral high-performance liquid chromatography (HPLC) into its enantiomers, and all four inherently chiral bambusuril pairs (two Pr 4 Me 4 BU[4] and two Bn 4 Me 4 BU[4] stereoisomers, 4b, 4d, 5b, and 5d) were clearly observed by 1 H NMR spectroscopy with the aid of (R)-BINOL as a chiral solvating agent. This latter methodology provides a rapid and powerful approach for investigating the enantiopurity of inherently chiral cavitands, which complements and augments the conventional chromatographic approaches.

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Section: Introductionmentioning

confidence: 99%