Phosphoramidite Ligands in Iridium-Catalyzed Allylic Substitution

✍ Scribed by Damien Polet; Alexandre Alexakis; Karine Tissot-Croset; Clémence Corminboeuf; Klaus Ditrich

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 468 KB
• Volume: 12
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200501180

✦ Synopsis

Abstract

A new phosphoramidite ligand was used in the iridium‐catalyzed allylic substitution reaction. This permitted high regio‐ and enantioselectivities on a wide variety of substrates and nucleophiles. Because of the stereospecificity of the reaction obtained by using branched substrates, a kinetic resolution reaction was attempted. The origin of the impressive efficiency of this ligand in terms of kinetics was explored in detail, as was the role of the substituent in the ortho‐position of the amine moiety.