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
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