Zirconium-Mediated Coupling Reactions of Amines and Enol or Allyl Ethers: Synthesis of Allyl- and Homoallylamines

✍ Scribed by José Barluenga; Félix Rodríguez; Lucía Álvarez-Rodrigo; José M. Zapico; Francisco J. Fañanás

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 183 KB
• Volume: 10
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200305374

✦ Synopsis

Abstract

An easy and efficient zirconium‐mediated synthesis of allylamines from simple amines and enol ethers is described. This strategy also allows the synthesis of amino alcohol derivatives containing a Z double bond in their structure when 2,3‐dihydrofuran is used. Simple conventional modification of these amino alcohols leads to 2‐substituted piperidine derivatives. By applying this approach, a formal total synthesis of the alkaloid coniine is easily achieved from a protected butylamine. Finally, the zirconium‐mediated reaction of amines and allyl phenyl ether furnishes homoallylamines or amino ethers depending on the structure of the starting amine.