Synfacts 2009(2): 0186-0186  
DOI: 10.1055/s-0028-1087634
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Ni-Catalyzed Diastereoselective Coupling of Dienes and Aldehydes

Contributor(s): Mark Lautens, Praew Thansandote
H. Y. Cho, J. P. Morken*
Boston College, USA
Further Information

Publication History

Publication Date:
22 January 2009 (online)

Significance

A three-component coupling of dienes, aldehydes, and a diboron reagent allows for the synthesis of homoallylic alcohols with good diastereoselectivities. Although the yields are mostly moderate to low, the methodology can potentially be used for the synthesis of functionalized alcohols such as polyketides. Aromatic, aliphatic and α,β-unsaturated aldehydes can be used for the reaction. Notably, reaction with cis- and trans- dienes leads to the same stereoisomer.