Host pre-resolution versus self-resolution in the formation of helical tubulate inclusion compounds

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Abstract
Racemic samples of the dialcohol 2 are known to yield two distinct types of clathrate inclusion compounds on crystallisation. Smaller guests (such as dichloromethane or cyclohexane) are included in cages within the ellipsoidal clathrate lattice (constructed from both enantiomers of the host 2). Larger guests (such as carbon tetrachloride or fluorocyclohexane) are enclosed in parallel tubes as part of the helical tubulate lattice. This structure contains only one enantiomer of 2 as a consequence of a spontaneous self-resolution process. Enantiomerically pure samples of 2 have now been prepared and the inclusion type found to switch to the helical tubulate for the smaller guests. Some much larger guest molecules (such as t-butylcyclohexane), which were not included at all by racemic 2, now also form helical tubulate inclusion structures when the resolved dialcohol 2 is used. Thus pre-resolution of the host allows extension of helical tubulate guest inclusion in both size directions.

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