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Synfacts 2006(12): 1256-1256
DOI: 10.1055/s-2006-949502
DOI: 10.1055/s-2006-949502
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Aminophosphines with Axial Chirality for Asymmetric Catalysis
T. Mino*, Y. Tanaka, Y. Hattori, T. Yabusaki, H. Saotome, M. Sakamoto, T. Fujita
Chiba University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-949502-1.jpg)
Significance
The utility of phosphine-containing chiral ligands has been well established and a new type of axially chiral C(aryl)-N(amine) ligand is described. The authors use a simple procedure to access a family of these axially chiral ligands in racemic form. Next, they expertly employ a palladium source with existing chirality to generate diastereomers which are separable on a simple silica gel column. The palladium is then titrated off with ethylene diamine to yield the ligands optically resolved, both with >99% ee. Application of the ligands in the palladium-catalyzed allylic alkylation was then employed and all ligands gave ee values ≥89%.