Tetraaryladamantanes as co-crystallization chaperones

Single crystal X-ray diffraction is the leading method for the determination of absolute configuration. The method, however, requires crystalline samples of sufficient quality, which are often difficult to obtain for acyclic molecules. In particular, this holds for highly flexible and low weight molecules that are liquid at room temperature. A new chaperone-aided crystallization method based on tetraaryladamantanes has delivered high quality co-crystals in a fair number of cases, allowing for the determination of the stereochemistry of liquid analytes. In contrast to other methods, the chaperone-aided crystallization can also be applied to molecules lacking functional groups.

The adamantane chaperone approach adds an important tool to the toolbox for both synthetic organic chemists and crystallographers, facilitating the investigation of organic molecules, such as new natural products, synthetic intermediates, pharmaceutically active ingredients, and fragrances. The co-crystallization is easy to apply and crystals suitable for the determination of absolute configuration are typically obtained within a few hours. With modern X-ray instrumentation the method can provide very fast access to the full 3D structure of a difficult class of organic and possibly inorganic analytes.

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