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- Title
Absolute Configuration Assignment from Optical Rotation Data by Means of Biphenyl Chiroptical Probes.
- Authors
Vergura, Stefania; Scafato, Patrizia; Belviso, Sandra; Superchi, Stefano
- Abstract
A non‐empirical approach for the assignment of the absolute configuration of chiral 2‐alkyl‐substituted carboxylic acids and primary amines by [α]D measurements has been developed. The method requires the conversion of the chiral acids or amines into the corresponding 4,4′‐disubstituted biphenylamides or biphenylazepines, respectively. In these derivatives a central‐to‐axial chirality transfer induces a preferred torsion in the biphenyl moiety revealed by the sign of the biphenyl A band in the ECD spectrum. By 4,4′‐substitution on the biphenyl moiety a redshift of the A band is obtained, leading to an increase of its relative contribution to optical rotation. This allows to reliably establish a direct correlation between the [α]D sign, the biphenyl twist and, then, the substrate absolute configuration. This approach thus constitutes a really practical and reliable method to assign the absolute configuration of chiral carboxylic acids and primary amines by simple and straightforward [α]D measurement, readily obtainable by a routine instrumentation like the polarimeter.
- Subjects
DIPHENYL; OPTICAL rotation; CARBOXYLIC acids; CHIRALITY; AMINES
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 22, p5682
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201806435