Abstract
Three camphor based crown ethers have been prepared, starting from (–)-(1R)-camphorquinone, in which 2- and 3-endo-substituents are used to regulate the availability of the endo-l8-crown-6 face for binding organic guests and the bridge head methyl group is available to impart enantioselectivity at the exo-face. The stereochemistry of the key intermediate 2-endo-3-endo-dimethyl bornane-2,3-diol (6) has been confirmed by a single crystal X-ray structure determination. Interactions between these crowns and antipodal phenylglycine salts have been probed using NMR and modelling techniques.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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