Synfacts 2011(9): 1006-1006  
DOI: 10.1055/s-0030-1260890
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Cr-Mediated Stereoselective Synthesis of α,β-Unsaturated Esters and Amides

Contributor(s): Paul Knochel, Andreas J. Wagner
H. Rodríguez-Solla*, C. Concellón, E. G. Blanco, J. I. Sarmiento, P. Díaz, R. G. Soengas
Universidad de Oviedo and Universidad de Santiago de Compostela, Spain
Further Information

Publication History

Publication Date:
19 August 2011 (online)


A novel chromium-mediated synthesis of carbohydrate-based polysubstituted (E)-α,β-unsaturated carboxylic esters and amides starting from a range of sugar aldehydes and α,α-dichlorocarbonyls is disclosed. In a mechanistic proposal, a sequential chromium-promoted aldol reaction and stereoselective β-elimination are the key steps of this transformation.