Synfacts 2011(12): 1325-1325  
DOI: 10.1055/s-0031-1289387
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Readily Accessible Diene Ligands for Enantioselective Conjugate Additions

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
B. M. Trost*, A. C. Burns, T. Tautz
Stanford University, USA
Further Information

Publication History

Publication Date:
18 November 2011 (online)

Significance

Chiral dienes as ligands in transition-metal catalysis received quite a bit of attention in recent years; however, ligand availability often limits the potential of the developed methods. This paper reports a convenient synthetic approach towards 2 and a library of related ligands via palladium-catalyzed asymmetric allylic alkylation (Pd-AAA). A palladium complex of 2 was successfully used in the conjugate addition of boronic acids to α,β-unsaturated ketones; the corresponding products were obtained with 73-99% yields and 54-92% ee.