The preparation and application of optically active organophosphorus compounds

Abstract

Racemic acyclic phosphine oxides were separated into their enantiomers applying classical resolution methods based on complexation with chiral host molecules. The preparation of chloro-3-phospholenium chlorides was elaborated by the reaction of 3-phospholene oxides with oxalyl chloride. The cyclic chlorophosphonium salts were key intermediates, as they could be converted to the corresponding 3-phospholene boranes. Moreover, these reactive intermediates could be reacted with chiral alcohols, which enabled us to develop a dynamic resolution of 3-phospholene oxides based on the formation of covalent diastereomeric intermediates. P-Stereogenic phosphine oxide pre-catalysts showed promising enantioselectivity values in a catalytic Wittig-reaction.

Graphical Abstract

Keywords:

• P-stereogenic
• phosphine oxide
• halophosphonium salt
• optical resolution
• enatioselective catalytic Wittig reaction

Additional information

Funding

National Research, Development and Innovation Office – NKFIH (Grant No. OTKA PD 116096).