High‐Throughput Assay for Enantiomeric Excess Determination in 1,2‐ and 1,3‐Diols and Direct Asymmetric Reaction Screening

A simple and efficient method for determination of the yield, enantiomeric/diasteriomeric excess (ee/de), and absolute configuration of crude chiral diols without the need of work‐up and product isolation in a high throughput setting is described. This approach utilizes a self‐assembled iminoboronat...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2017-07, Vol.23 (42), p.10222-10229
Main Authors: Shcherbakova, Elena G., Brega, Valentina, Lynch, Vincent M., James, Tony D., Anzenbacher, Pavel
Format: Article
Language:English
Subjects:
Absolute configuration
Assaying
asymmetric catalysis
Asymmetric synthesis
Asymmetry
Atorvastatin
Benzil
Chemistry
Covalence
Diols
enantiomeric excess
Feasibility studies
Fluorescence
High-throughput screening
Hydrogenation
Hypercholesterolemia
Real time
Screening
Self-assembly
Tryptophan
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A simple and efficient method for determination of the yield, enantiomeric/diasteriomeric excess (ee/de), and absolute configuration of crude chiral diols without the need of work‐up and product isolation in a high throughput setting is described. This approach utilizes a self‐assembled iminoboronate ester formed as a product by dynamic covalent self‐assembly of a chiral diol with an enantiopure fluorescent amine such as tryptophan methyl ester or tryptophanol and 2‐formylphenylboronic acid. The resulting diastereomeric boronates display different photophysical properties and allow for fluorescence‐based ee determination of molecules containing a 1,2‐ or 1,3‐diol moiety. This method has been utilized for the screening of ee in a number of chiral diols including atorvastatin, a statin used for the treatment of hypercholesterolemia. Noyori asymmetric hydrogenation of benzil was performed in a highly parallel fashion with errors
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201701923