Stereoselective synthesis of a set of two functionalized (E)-alkene dipeptide isosteres of L-amino acid-L-Glu and L-amino acid-D-Glu

Treatment of N-arylsulfonyl-gamma,delta -cis- or -trans-gamma,delta -epimin o (E)-alpha,beta -enoates with HCl-1,4-dioxane affords regio- and stereo-se lective ring-opened products, delta -aminated gamma -chloro-alpha,beta -eno ates. This ring-opening reaction provides a useful method for the stereosel ective synthesis of a set of diastereomeric (L-Xaa, L-Glu)-type and (L-Xaa, D-Glu)-type (E)-alkene dipeptide isosteres (EADIs) from a single substrate of gamma,delta -epimino (E)-alpha,beta -enoate using organozinc-copper rea gents.