Repository logo
 

A non-chiral lithium aluminate reagent for the determination of enantiomeric excess of chiral alcohols

Accepted version
Peer-reviewed

Repository URI

https://www.repository.cam.ac.uk/handle/1810/262879

Repository DOI

https://doi.org/10.17863/CAM.8170

Files

Accepted version (861.97 KB)

Type

Article

Change log

Authors

Garcia Rodriguez, Raul  ORCID logo  https://orcid.org/0000-0003-0699-3894
Bond, AD 
Wright, DS 

Abstract

Here we illustrate a new method for the rapid determination of ee’s of chiral alcohols using the thermally-stable, non-chiral lithium aluminate reagent [EtAl(6-Me-2-py)3Li] (1). In situ reaction of the alcohols with 1 produces robust dimers in solution, present as diastereomeric pairs (SS/RR and RS) with distinct resonances in their 1H and 7Li NMR spectra. The ee can be calculated simply from integration of the 1H and/or 7Li NMR spectra.

Description

Keywords

3405 Organic Chemistry, 34 Chemical Sciences

Journal Title

Chemical Communications

Conference Name

Journal ISSN

1359-7345
1364-548X

Volume Title

53

Publisher

Royal Society of Chemistry

Publisher DOI

https://doi.org/10.1039/c6cc09671a

Rights

http://www.rioxx.net/licenses/all-rights-reserved
Sponsorship
Engineering and Physical Sciences Research Council (EP/K039520/1)
We thank the EU for a Marie Curie Intra European Fellowship within the seventh European Community Framework Programme (R. G. R.) and an Advanced Investigator Award (D. S. W.). We also thank the Fonds der Chemischen Industrie and the Studienstiftung des deutschen Volkes (Scholarships for S. H.).

Collections

Scholarly Works - Chemistry
Symplectic mapped items for data match