Photocatalyzed Reductive Ring-Opening of γ-(2-Chloroaziridinyl)acrylates Using Dihydropyridines: Access to (Z)-Chloroalkene Dipeptide Isosteres
Related Experiment Video
Updated: Jun 10, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Chihiro Iio1, Mio Takeda2, Harui Miyata2
1Graduate School of Medical Photonics, Shizuoka University, 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8011, Japan.
Abstract:
Herein, we report a visible-light photoredox-catalyzed reductive ring-opening of γ-(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 α-alkyl substituents. This method provides an alternative to conventional organocuprate-mediated CADI synthesis.
Related Concept Videos
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Acid-Catalyzed Ring-Opening of Epoxides
Base-Catalyzed Ring-Opening of Epoxides
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)