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Synthesis of 2‐Methylresorcinol‐Based Deepened Cavitands with Chiral Inlet Bearing Steroidal Moieties on the Upper Rim
Author(s) -
Nagymihály Zoltán,
Wölfling János,
Schneider Gyula
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001728
Subject(s) - chemoselectivity , sonogashira coupling , chemistry , carbonylation , carbon monoxide , cavitand , combinatorial chemistry , substrate (aquarium) , high pressure , catalysis , organic chemistry , molecule , palladium , supramolecular chemistry , oceanography , engineering physics , engineering , geology
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 tetra‐carboxamides 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.