Chiral 1,10-Phenanthroline-Bridged Calix[6]arenes

✍ Scribed by Serge Konrad; Michael Bolte; Christian Näther; Ulrich Lüning

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 341 KB
• Volume: 2006
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200600295

✦ Synopsis

Abstract

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)