Department of Organic Chemistry, University of Chemistry and Technology, Prague (UCTP) , Technická 5, 166 28 Prague 6, Czech Republic.
Solid State Department, UCTP , 166 28 Prague 6, Czech Republic.
Org Lett. 2017 Jun 2;19(11):2933-2936. doi: 10.1021/acs.orglett.7b01170. Epub 2017 May 22.
The mercuration of calix[4]arene immobilized in the cone conformation allowed the introduction of an amino group at the meta position of the basic skeleton. Acylation and subsequent intramolecular Bischler-Napieralski-type cyclization led to a novel type of bridged calixarene containing a seven-membered ring. These compounds with an enlarged and rigidified cavity represent a unique and inherently chiral system that may potentially be applicable for the design of chiral receptors. The absolute configuration of one enantiomer, obtained by resolution of the racemate using chiral HPLC, was assigned by single-crystal structure determination.
杯[4]芳烃的汞化作用固定在锥型构象中，允许在碱性骨架的间位引入氨基。酰化和随后的分子内 Bischler-Napieralski 型环化反应导致了一种新型的桥连杯芳烃，其中含有一个七元环。这些具有扩大和刚性化空腔的化合物代表了一种独特的、固有手性的体系，可能有潜力应用于手性受体的设计。对通过手性 HPLC 拆分外消旋体得到的一个对映异构体的绝对构型，通过单晶结构测定进行了确定。
