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Chiral 1,10‐Phenanthroline‐Bridged Calix[6]arenes
Author(s) -
Konrad Serge,
Bolte Michael,
Näther Christian,
Lüning Ulrich
Publication year - 2006
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.200600295
Subject(s) - chemistry , cyclopropanation , calixarene , indene , phenanthroline , reagent , copper , enantioselective synthesis , styrene , medicinal chemistry , catalysis , stereochemistry , polymer chemistry , organic chemistry , molecule , copolymer , polymer
Several approaches to chiral derivatives of the 1,10‐phenanthroline‐bridged calix[6]arene 3 have been investigated, and seven new chiral calix[6]arenes have been synthesized. The C 2 ‐symmetric axially chiral bimacrocycle 5 has been synthesized as racemic mixture; calixarenes 8 , 14 , 18 , 19 , 20 and 21 carrying chiral substituents (camphorsulfonyl, myrtanyl) have been prepared using enantiomerically pure reagents. Three chiral bimacrocycles 5 , 19 and 20 have also been analyzed by X‐ray analyses. All compounds have been tested as ligands for copper ions in the Cu I ‐catalyzed cyclopropanation of styrene and indene.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)