The Design of Resolving Agents. Chiral Cyclic Phosphoric Acids

Article abstract of DOI:10.1021/jo00223a018

A systematic investigation has been started with the twofold purpose of synthesizing efficient resolving agents and of gaining an insight into the factors that contribute to successful resolutions.We report on the synthesis, resolution, and application of a number of chiral cyclic phosphoric acids.Among these acids, 4-(2-chlorophenyl)-5,5-dimethyl-2-hydroxy-1,3,2-dioxaphosphorinane 2-oxide (7A) is an efficient resolving agent, being useful for the resolution of amines and amino acids.Acid chloride 20 is a useful reagent for the determination of the ee of chiral amines.The absolute configuration of (-)-7A was determined through an X-ray structure determination of its salt with (-)-(p-hydroxyphenyl)glycine.