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.
Org Lett. 2012 Jul 20;14(14):3628-31. doi: 10.1021/ol301420t. Epub 2012 Jul 3.
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.
杯芳烃系列中的亲电芳香取代反应是一种成熟的方法,只能得到对位取代衍生物。本文描述了汞化反应导致间位取代杯[4]芳烃的前所未有的区域选择性。这些化合物代表了经典杯芳烃化学中的一种新型取代模式,为基于杯芳烃的固有手性受体的直接合成开辟了道路。