Download PDF
Synfacts 2010(6): 0680-0680  
DOI: 10.1055/s-0029-1219864
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Applications of Acyclic Chiral Diene Ligands

Contributor(s): Mark Lautens, Chit Tsui
X. Hu, Z. Cao, Z. Liu, Y. Wang, H. Du*
Beijing National Laboratory of Molecular Sciences, P. R. of China
Further Information

Publication History

Publication Date:
20 May 2010 (online)

    Permissions and Reprints

Significance

Chiral bicyclic diene ligands have been successfully employed in asymmetric catalysis, however, their syntheses are often quite challenging. The authors present a simple one-step synthesis of an acyclic chiral diene ligand 3 via palladium(0)-catalyzed asymmetric diamination of 1,5-hexadiene (1) in excellent ee. This type of ligands have been shown to be effective in rhodium-catalyzed asymmetric 1,4-addition of phenylboronic acid to 2-cyclohexenone. Excellent conversion and up to 85% ee can be obtained with selected ligands.