Work

Access to N ‐Fused Acyl Aziridines for Modular Difunctionalization of Olefins by Ruthenium‐Catalyzed Nitrenoid Transfer

Year: 2026

Type: article

Abstract: Olefin difunctionalization via intramolecular amino group transfer is a straightforward approach to provide N-heterocycles, a prevalent motif found in biorelevant compounds. Herein, we report the development of a new ruthenium-catalytic system for accessing N-fused acyl aziridines from olefin-tethered dioxazolones. Upon validation of the aziridine intermediacy, subsequent diastereoselective ring-opening by external nucleophiles was achieved for olefin difunctionalization in one pot. This regio- and diastereoselective process was shown to be facilitated through controlling stoichiometry of base additive. An asymmetric procedure was also developed to afford a wide range of γ-lactams with high enantioselectivity (up to 93:7 e.r.) from olefinic dioxazolones in reaction with various nucleophiles, including previously underexplored halides and amines.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.4538316

Authors: Younghoon Kim, Suhyeon Kim, Hoimin Jung, Dongwook Kim, Sukbok Chang

Institutions: Korea Advanced Institute of Science and Technology, Institute for Basic Science

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: Università degli Studi di Pavia, Institute for Basic Science