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Concave Annelated Terpyridines
Author(s) -
Lüning Ulrich,
Liebig Timo
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101356
Subject(s) - chemistry , cyclopropanation , metathesis , stereoselectivity , terpyridine , reactivity (psychology) , boronic acid , aryl , ring closing metathesis , organic chemistry , copper , stereochemistry , medicinal chemistry , combinatorial chemistry , catalysis , polymerization , medicine , alkyl , alternative medicine , pathology , metal , polymer
Bimacrocyclic concave annelated terpyridines were generated from a U‐shaped nonmacrocyclic tetraalkene precursor by ring closing metathesis followed by hydrogenation. The U‐shaped precursor was synthesized by condensing two aryl‐tetrahydroquinolones with Eschenmoser's salt. The quinolones themselves were accessible by coupling a 2‐chloroquinolone with a bis‐alkenyloxy‐substituted boronic acid. The concave terpyridine was tested for reactivity and stereoselectivity in a copper(I)‐catalyzed cyclopropanation.