Diastereomeric resolution rationalized by phase diagrams under the actual conditions of the experimental process

Rational approach to the selection of conditions for diastereomeric resolution of chiral amines by diacid resolving agents

“…For given resolution conditions, resolution yield (Y) and enantiomeric excess (ee) can be calculated from the eutectic composition, avoiding the need for obtaining the complete ternary phase system, and so determination of eutectic points can also be used for the selection of the resolution system. [8][9][10][11] During selection of the resolving agent, it is important to note that the main advantage of the diastereomeric resolution is the relatively low costs of the process, which are mainly associated with the resolving agent costs. Looking at the commonly available resolving agents, tartaric acid and its derivatives are the most popular choice for resolving chiral bases, accounting, for 1368 resolutions of chiral bases reported by Kozma.…”

Design of Resolving Agents Based on Crystal Engineering

“…6 On the other hand, the early systematic and thorough studies by Jaques, Collet and their coworkers on diastereomeric resolution clarified the correlation between the physical properties of diastereomeric salts and the efficiency of resolution based on the phase diagram. 2,7 Moreover, subsequent work by Wynberg's group suggested the possibility that studying the crystal structures of a series of a diastereomeric salts would be helpful for understanding resolution phenomena at a molecular level. 8 Is it possible to design rationally a resolving agent or a derivatizing agent simply from the molecular structure of the target racemate?…”

Recrystallization of Enantiomers from Conglomerates

“…Let us just mention the Marckwald's method (Marckwald, 1896), the Pope and Peachey's method (Pope & Peachey, 1899) and more recently the Dutch resolution (Vries et al, 1998), (Kaptein et al, 2000). Note also that the accurate determination of the phase diagrams under the conditions of the experimental process allows an optimization of the resolution (Marchand et al, 2004). Even imperfect (a yield close to 100% is rarely obtained), this method most often fits industrial and laboratories requirements.…”