Synfacts 2009(8): 0886-0886  
DOI: 10.1055/s-0029-1217439
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

A Copper-Imidazoline-Aminophenol Complex for Asymmetric 1,4-Additions

Contributor(s): Mark Lautens, Praew Thansandote
N. Yokoyama, T. Arai*
Chiba University, Japan
Further Information

Publication History

Publication Date:
23 July 2009 (online)

Significance

A new nitro-substituted imidazoline-aminophenol-copper complex is shown to be a powerful and general Lewis acid for the 1,4-addition reaction of pyrroles and indoles with nitro-alkenes. The resulting adducts can undergo NO2 reduction followed by Pictet-Spengler cyclization in good yields and diastereoselectivities.