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