Format

Send to

Choose Destination
Org Lett. 2019 Apr 5;21(7):2412-2415. doi: 10.1021/acs.orglett.9b00707. Epub 2019 Mar 14.

Troponoid Atropisomerism: Studies on the Configurational Stability of Tropone-Amide Chiral Axes.

Author information

1
Department of Chemistry , Brooklyn College, The City University of New York , Brooklyn , New York 11210 , United States.
2
PhD Program in Chemistry , The Graduate Center of the City University of New York , New York , New York 10016 , United States.
3
Department of Chemistry , Yale University , New Haven , Connecticut 06520-8107 , United States.

Abstract

Configurationally stable, atropisomeric motifs are an important structural element in a number of molecules, including chiral ligands, catalysts, and molecular devices. Thus, understanding features that stabilize chiral axes is of fundamental interest throughout the chemical sciences. The following details the high rotational barriers about the Ar-C(O) bond of tropone amides, which significantly exceed those of analogous benzamides. These studies are supported by both experimental and computational rotational barrier measurements. We also report the resolution of an axially chiral α-hydroxytropolone amide into its individual atropisomers, and demonstrate its configurational stability at physiological pH and temperatures over 24 h.

PMID:
30869521
PMCID:
PMC6504963
[Available on 2020-04-05]
DOI:
10.1021/acs.orglett.9b00707

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center