Synfacts 2006(8): 0821-0821  
DOI: 10.1055/s-2006-942013
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Construction of Quaternary Carbon Stereocenters

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
R. Shintani, W.-L. Duan, T. Hayashi*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
21 July 2006 (online)

Significance

The authors have found a fine protocol for the construction of all-carbon chiral quaternary stereocenters. They discovered that the use of the bidentate phosphine ligand (R)-H8-BINAP provides opposite regioselectivity to the diene ligands (R,R)-Bn-bod and (R,R)-Ph-bod. High enantio­selectivities for the addition of a variety of arylboronic acids were obtained. The regioselectivity was as high as >98:2 (1:2) in some cases. Various electron-donating as well as electron-withdrawing groups on the aryl moiety of the arylboronicacids were tolerated.