Jump to main content
Jump to site search


Central-to-axial chirality induction in biphenyl chiroptical probes for the stereochemical characterization of chiral primary amines

Author affiliations

Abstract

Flexible biphenyls have been applied as efficient and practical chiroptical probes for absolute configuration assignment to chiral primary amines. The mechanism of the central-to-axial chirality transfer from the amine moiety to the conformationally flexible biphenyl system has been determined by NMR and computational studies. This allowed proposing a general non-empirical rule in order to establish, simply by looking at the sign of the 250 nm A band in the ECD spectrum of the biphenyl derivative, the torsion of the biphenyl and thus the absolute configuration of the amine. The method proved to be very reliable and sensitive, allowing treatment of samples on the μmol scale and permitting the simultaneous determination of the amine sample's absolute configuration and enantiopurity.

Graphical abstract: Central-to-axial chirality induction in biphenyl chiroptical probes for the stereochemical characterization of chiral primary amines

Back to tab navigation

Supplementary files

Publication details

The article was received on 07 Nov 2017, accepted on 18 Dec 2017 and first published on 18 Dec 2017


Article type: Paper
DOI: 10.1039/C7OB02730C
Citation: Org. Biomol. Chem., 2018, Advance Article
  •   Request permissions

    Central-to-axial chirality induction in biphenyl chiroptical probes for the stereochemical characterization of chiral primary amines

    S. Vergura, L. Pisani, P. Scafato, D. Casarini and S. Superchi, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02730C

Search articles by author

Spotlight

Advertisements