A [5]HELOL Analogue That Senses Remote Chirality in Alcohols, Phenols, Amines, and Carboxylic Acids
- 21 September 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (21) , 8497-8502
- https://doi.org/10.1021/jo0512913
Abstract
A route is developed to a structural analogue of [5]HELOL, a previously reported helically grooved sensor of remote chirality. It gives the material enantiomerically pure and in multigram quantities. The enantiomers of alcohols, phenols, amines, and carboxylic acids, even when their centers of chirality are remote from any functional groups, can be differentiated by 31P NMR spectroscopic analyses of their reaction products with the chlorophosphite of this material.Keywords
This publication has 23 references indexed in Scilit:
- Synthesis of New Chiral Aryl Diphosphite Ligands Derived from Pyranoside Backbone of Monosacharides and Their Application in Copper‐Catalyzed Asymmetric Conjugate Addition of Diethylzinc to Cyclic EnonesAdvanced Synthesis & Catalysis, 2004
- Preparation of 9,10‐Dimethoxyphenanthrene and 3,6‐Diacetyl‐9,10‐DimethoxyphenanthrenePublished by Wiley ,2003
- First Friedel−Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]HelicenesThe Journal of Organic Chemistry, 2000
- [5]HELOL Phosphite: A Helically Grooved Sensor of Remote ChiralityJournal of the American Chemical Society, 2000
- Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of HelicenesThe Journal of Organic Chemistry, 2000
- An Efficient Synthesis of Functionalized HelicenesJournal of the American Chemical Society, 1997
- On the Acetylation of Phenanthrene and 9‐chlorophenanthreneJournal für Praktische Chemie, 1989
- Syntheses and structural characteristics of new highly fluorinated di-tert-butyl-1,3,2,4-diazadiphosphetidinesInorganic Chemistry, 1987
- Dimere Naphthochinone, II. Einfache und regioselektive Synthese von Naphthohydrochinon‐monoalkylethern über 2,3‐DihydronaphthochinoneEuropean Journal of Organic Chemistry, 1980
- Photochemical reactions of .alpha.-ketophosphonatesThe Journal of Organic Chemistry, 1970