Synthesis of 2-Methylresorcinol-Based Deepened Cavitands with Chiral Inlet Bearing Steroidal Moieties on the Upper Rim

Nagymihály, Zoltán and Wölfling, János and Schneider, Gyula and Kollár, László (2020) Synthesis of 2-Methylresorcinol-Based Deepened Cavitands with Chiral Inlet Bearing Steroidal Moieties on the Upper Rim. ChemistrySelect. pp. 6933-6938. ISSN 2365-6549

Text chemsel20_6933.pdf Restricted to Repository staff only Download (4MB)

Abstract

A tetraiodocavitand, synthesised in conventional high-yielding reactions, was used as substrate in homogeneous catalytic reactions such as aminocarbonylation and Sonogashira reaction. 3α-Aminopregnane and 17α-ethinylandrostane derivatives were used as coupling agents, respectively. While the aminocarbonylation of the tetraiodocavitand carried out at low pressure carbon monoxide resulted in the formation of tetracarboxamides as major products, the high pressure carbonylation (40 bar CO) yielded the corresponding tetrakis(2-ketocarboxamides) with high chemoselectivity. The ethinyl functionality of the steroid enabled the facile cross-coupling with the cavitand possessing iodoarene functionalities.

Actions (login required)

Edit Item