Resolution of P-stereogenic P-heterocycles via the formation of diastereomeric molecular and coordination complexes (a review)

Abstract

TADDOL derivatives and the Ca²⁺-salts of tartaric acid derivatives were found to be versatile and generally applicable resolving agents for the preparation of the enantiomers of P-stereogenic heterocyclic phosphine oxides and phosphinates via the formation of the corresponding diastereomeric molecular and coordination complexes. A few of the diastereomeric intermediates were characterized by single crystal X-ray crystallography to gain insights into the binding mode of the corresponding heterocyclic phosphine oxide (“guest”) and the resolving agent (“host”) and to study the underlying phenomenon of enantiomeric recognition.