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Synfacts 2006(12): 1256-1256  
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

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Mino*, Y. Tanaka, Y. Hattori, T. Yabusaki, H. Saotome, M. Sakamoto, T. Fujita
Chiba University, Japan
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Publication History

Publication Date:
22 November 2006 (online)

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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%.