Abstract
In our work we have provided the lower rim of resorc[4]arenes with stereogenic centers as well as with functional groups. For
the synthesis of these lower rim functionalized chiral resorc[4]arenes we have used aldehydes derived from citronellal
and carvone. In general, the functional group was introduced into the aldehyde compound
prior to the final cyclization step. In the case of substitution of the functional
group by chloride ions during the cyclization step under standard conditions (HCl-EtOH,
Δ), hydrochloric acid was replaced by the conjugated acid of the functional group.
Another strategy is the introduction of the iodo group at the lower rim of a resorc[4]arene, which can be easily substituted by good nucleophiles and mild
bases without protection of the upper rim.
Key words
resorcarenes - macrocycles - chirality - molecular recognition - aldehydes - cyclizations
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