Highly regioselective synthesis of chiral diamines via a Buchwald–Hartwig amination from camphoric acid and their application in the Henry reaction. (29th May 2014)

• Record Type: Journal Article
• Authors: Uzarewicz‐Baig, Magdalena; Koppenwallner, Maximilian; Tabassum, Sobia; Wilhelm, René
• Is Part Of: Applied organometallic chemistry. Volume 28:Number 7(2014:Jul.)
• Page Start: 552
• Page End: 558
• Publication Date: 2014-05-29
• Subjects: Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.3162
• Languages: English
• ISSNs: 0268-2605

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>In this work the synthesis of new asymmetric diamine ligands from camphoric acid is described. The new diamines can be directly prepared in a <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">regioselective arylation</named-content> of the less hindered primary amine group of (+)‐<italic>cis</italic>‐1, 2, 2‐trimethylcyclopentane‐1, 3‐diamine via a <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Buchwald–Hartwig amination</named-content> in high yields. The resulting diamines incorporate a secondary and primary amine group and were successfully applied as ligands in a copper‐catalyzed <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Henry reaction</named-content>. Copyright © 2014 John Wiley &amp; Sons, Ltd.</p> </abstract>