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Org Lett. 2012 Jul 20;14(14):3628-31. doi: 10.1021/ol301420t. Epub 2012 Jul 3.

Unprecedented meta-substitution of calixarenes: direct way to inherently chiral derivatives.

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Department of Organic Chemistry, Prague Institute of Chemical Technology , Technicka 6, 166 28 Prague 6, Czech Republic, Institute of Organic Chemistry and Biochemistry, v.v.i. Academy of Sciences of the Czech Republic , Flemingovo 2, 166 10 Prague 6, Czech Republic, Institute of Chemical Process Fundamentals, v.v.i. Academy of Sciences of the Czech Republic , Rozvojova 135, 165 02 Prague 6, Czech Republic, and Department of Inorganic Chemistry, Charles University , Hlavova 8, 128 43 Prague 2, Czech Republic.


Electrophilic aromatic substitution in the calix[n]arene series is a well-established procedure leading exclusively to para-substituted derivatives. An unprecedented regioselectivity of the mercuration reaction leading to the meta-substituted calix[4]arenes is described. These compounds represent a new type of substitution pattern in classical calixarene chemistry and open the door for the straightforward synthesis of inherently chiral receptors based on calixarenes.

[Indexed for MEDLINE]

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