Diastereoselective synthesis of 5-iminooxazolines and their subsequent transformation to α,α-disubstituted dipeptide esters: a formal [4+1] cycloaddition reaction of cyclohexyl isocyanide and Z-alkyl-α-benzoyl amino-acrylates

A novel atom economical diastereoselective synthesis of 5-iminooxazolines and their subsequent transformation to alpha,alpha-disubstituted dipeptide esters is described. Heating a mixture of cyclohexyl isocyanide and Z-alpha-benzoyl amino-acrylic acid alkyl esters under solvent-free conditions, afforded 5-iminooxazolines, which, upon specifications provided alpha,alpha-disubstituted dipeptide esters in good yield. (C) 2012 Elsevier Ltd. All rights reserved.