Time dependent efficiency of optical resolution of aminooxiranes with O,O′-dibenzoyl-(R,R)-tartaric acid

Crystallization time dependent efficiencies of optical resolutions of two aminooxirane derivatives have been investigated. Time-scaled experiments demonstrated that efficient chiral discrimination of aminooxirane enantiomers by the resolving agent develops in slow, diffusion controlled exchange of the enantiomers between the solution and the precipitated salt of an enantiomeric mixture and the resolving agent. Comparison of the determined absolute configurations of the resolved aminooxiranes showed that quasi enantiomers of the structurally similar two model compounds crystallized with the same resolving agent from ethyl acetate.