ChemInform Abstract: Nickel-Catalyzed Asymmetric Multiple-Component Tandem Coupling. Effects of Simple Monodentate Oxazolines as Chiral Ligands.

✍ Scribed by Shin-ichi Ikeda; Dong-Mei Cui; Yoshiro Sato

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199936032

✦ Synopsis

Nickel-Catalyzed Asymmetric Multiple-Component Tandem Coupling. Effects of Simple Monodentate Oxazolines as Chiral Ligands.

-Chiral monodentate oxazoline ligands (I), especially the tert-butyl derivative (Ic), serve as effective ligands in the nickel-catalyzed cascade coupling of enones (II) and (VIII) with acetylenes, Me 2 Zn, and Me 3 SiCl. The reaction affords the corresponding γ-alkenyl silyl enol ethers which are subsequently hydrolyzed to give β-alkenyl ketones (V), (VII), and (IX). The cascade type reaction is applicable to internal as well as terminal acetylenes and to α,β-unsaturated aldehydes.