Resolution of acyclic phosphine oxides with TADDOL- and tartaric acid derivatives

Abstract

The resolution methods previously developed for the enantioseparation of heterocyclic phosphine oxides were extended to dialkyl-aryl-, diaryl-alkyl- and triarylphosphine oxides. The resolution of the phosphine oxides were elaborated with TADDOL-derivatives or with the acidic Ca²⁺-salts of the (R,R)-O,O’-dibenzoyl- and (R,R)-O,O’-di-p-toluoyl-tartaric acid. The main parameters influencing the efficiency of the resolution procedures were also optimized. Moreover, a correlation was found between the efficiency of the resolution and molecular structure. In a few instances, the purification and the racemization possibilities of the enantiomeric mixtures were also investigated.

Graphical Abstract

Keywords:

• Acyclic phosphine oxides
• P-stereogenic
• optical resolution
• TADDOL derivatives
• tartaric acid derivatives

Additional information

Funding

This work was supported by the National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096).