Synthesis of optically pure calix[4]arenes derived from Evans oxazolidinone and/or pyranose
- 1 October 2022
- journal article
- Published by Peertechz Publications Private Limited in Open Journal of Chemistry
- Vol. 8 (1), 001-007
- https://doi.org/10.17352/ojc.000028
Abstract
Eight new optically pure calixarene derivatives, in which their lower rims were substituted with Evans oxazolidinone or pyranose moieties, are described. All macrocycles were fully characterized by NMR spectroscopy, optical rotation, and elemental analysis. The introduction of chiral auxiliaries reduced the symmetry of the macrocycle as observed by NMR. Stereospecific alkylation on the Evans oxazolidinone moiety allowed the asymmetric introduction of a methyl substituent near a phenolic position of the macrocycle.Keywords
This publication has 24 references indexed in Scilit:
- Inherently chiral concave molecules—from synthesis to applicationsChemical Society Reviews, 2010
- Calixarene and Calixresorcarene Glycosides: Their Synthesis and Biological ApplicationsChemical Reviews, 2010
- A brief review ofCn-symmetric calixarenes and resorcinarenesSupramolecular Chemistry, 2010
- The Use of Calixarenes in Metal-Based CatalysisChemical Reviews, 2008
- Acylation, Diastereoselective Alkylation, and Cleavage of an Oxazolidinone Chiral AuxiliaryJournal of Chemical Education, 2008
- Calix[4]arene-derived diphosphines, diphosphinites and diphosphites as chelating ligands for transition metal ions. Encapsulation of silver(I) in a calix-crown diphosphiteJ. Chem. Soc., Dalton Trans., 2001
- Phosphorus-containing calixarenesRussian Chemical Reviews, 1998
- Synthesis and Properties of O‐Glycosyl Calix[4]Arenes (Calixsugars)Chemistry – A European Journal, 1997
- Sugar Calixarenes: Preparation of Calix[4]arenes Substituted at the Lower and Upper Rims with O‐Glycosyl GroupsAngewandte Chemie, 1995
- Asymmetric alkylation reactions of chiral imide enolates. A practical approach to the enantioselective synthesis of .alpha.-substituted carboxylic acid derivativesJournal of the American Chemical Society, 1982