Dutch Resolution is the term given to the use of mixtures (families) of resolving agents in classical resolutions. In this status report an overview is given of the latest results and new (possible) families of resolving agents are introduced. The concept of families is discussed as well as the factors that come into play on use of families. Practical aspects of Dutch Resolution in particular and resolutions in general are discussed.
Schwarze Schafe in der Familie? Für einen kombinatorischen Prozess zur Racematspaltung über die Trennung diastereomerer Salze mithilfe von Gemischen („Familien“) strukturell verwandter Reagentien (Beispiele sind gezeigt) wurde der Begriff „Dutch Resolution“ geprägt. Einige Familienmitglieder werden nicht in die Salze eingebaut; offensichtlich verhindern sie die Keimbildung. Daraus ergibt sich eine vereinfachte Zwei‐Komponenten‐Methode mit hohen Erfolgsquoten schon zu Beginn des (iterativen) Prozesses.
Die Racematspaltung revolutionieren könnte das hier vorgestellte kombinatorische Verfahren, bei dem Gemische („Familien”︁) strukturell und stereochemisch verwandter Reagentien mit den zu trennenden racemischen Säuren oder Basen umgesetzt werden. Die in üblicherweise einem Schritt gebildeten diastereomeren Salze fallen fast immer rasch aus, Ausbeuten und Enantiomerenüberschüsse sind gut bis hervorragend. Auch Reagensgemische mit racemischen oder achiralen Komponenten wurden entwickelt.
An overview is given of the principles of Pasteur resolutions via separation of diastereomeric salts.Thereafter, primary nucleation processes of (chiral) organic compounds in supersaturated solution are consideredfollowed by crystal growth in the presence of tailor-made additives. A representative example of a DutchResolution is presented, the concept of families of resolving agents is defined and examples are given.The phenomenon of reversed Dutch Resolution, resolution of mixtures of families of racemates, is illustrated.The roles of both solid solution formation and nucleation inhibition in Dutch Resolution are discussed.The work is concluded with the results of a broadly based search for nucleation inhibitors for phenylethylamine as resolving agent. This search can serve as a model for the discovery of nucleation inhibitorsfor other resolving agents. The specific role of bifunctional family members of resolving agents as possiblenucleation inhibitors is also discussed.
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