Atropisomerism at the carbon–phosphorus bond
Abstract
The feasibility of halting the rotation about a C–P bond is reported. At the outset, atropisomers with configurationally stable stereogenic C–P axes were synthesized in the form of triptycyl phosphine oxides with threefold stereogenicity. Their bond rotational profile revealed that each of the three barriers amounts to more than 115 kJ/mol, which permits the isolation of the antiperiplanar and the two enantiomeric synclinal C–P atropisomers under ambient conditions. Furthermore, the feasibility of their atroposelective synthesis by desymmetrization was established to catalytically control the configuration of stereogenic C–P axes. A first application of the synthesized C–P atropisomers was demonstrated by determining the absolute configuration of a protected amino acid.
Fields of Study & Subjects
Axial and Atropisomeric Chirality Synthesis
Asymmetric Synthesis and Catalysis
Supramolecular Chemistry and Complexes
Publication details
- Journal / source
- Chem
- Publisher
- Elsevier BV
- Volume
- 12
- Issue
- 10
- Pages
- 103076–103076
- Publication date
- 1 May 2026
- Language
- EN