Access to pyrrolines and fused diaziridines by selective radical addition to homoallylic diazirines
Zhigang Ma1, Xinxin Wu1*（吴新鑫）,Haotian Li1, Zhu Cao2 , Chen Zhu1,2（朱晨）
1 Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.
2Frontiers Science Center for Transformative Molecules, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
Chem. Sci., 2024, 15, 1879
Abstract: Pyrroline derivatives are common in bioactive natural products and therapeutic agents. We report here a synthesis of pyrrolines and fused diaziridines by divergent radical cyclization of homoallylic diazirines, which can serve as an internal radical trap and a nitrogen source. This reaction proceeds by selective radical addition to C=C or N=N bonds followed by intramolecular cyclization. Frontier molecular orbital analysis provides a deep insight into the origin of the selectivity. The reaction demonstrates a new cyclization mode, broad functional group compatibility and high product diversity, and reveals a much broader chemical space for diazirine studies.
链接： //pubs.rsc.org/en/content/articlelanding/2024/sc/d3sc04886a
