Photocatalyzed Reductive Ring-opening of g-(2-Chloroaziridinyl)acrylates Using Dihydropyridines: Access to (Z)-Chloroalkene Dipeptide Isosteres.

Herein, we report a visible-light photoredox-catalyzed reductive ring-opening of g-(2-chloroaziridinyl)acrylates using Hantzsch esters,providing catalytic access to (Z)-chloroalkene dipeptide isosteres (CADIs). The reaction proceeds under mild conditions with high Z-selectivity and broad functional group tolerance, affording Xaa–Gly-type (Z)-CADIs that mimic the trans-amide geometry. Furthermore, the use of 4-alkyl Hantzsch esters enables direct access to CADIs bearing a-alkyl substituents. This method provides an alternative to conventional organocuprate-mediated CADI synthesis.

J. Org. Chem., accepted.