Copper(II)-Catalyzed Asymmetric (3+3) Annulation of Diaziridines with Oxiranes

作者：Ying Hu, Heng-Bin Yu, Tian Yin, Ming‐Sheng Xie, Hai‐Ming Guo · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c00064 · 被引用次数：7 · 研究领域：Synthesis and Catalytic Reactions、Catalytic C–H Functionalization Methods、Cyclopropane Reaction Mechanisms

Highly asymmetric (3+3) annulation of diaziridines with oxiranes via C–N bond cleavage in diaziridine was achieved under 10 mol % of chiral copper(II) complex as the catalyst under mild reaction conditions. With Cu(OTf) 2 as the Lewis acid and C 1 -symmetric imidazolidine-pyrroloimidazolone pyridine as the ligand, diverse tetrahydro-[1,3,4]-oxadiazines were obtained by stereospecific C–N/C–O bond formation in moderate to good yields (up to 93% yield) and high diastereo- (>20:1 dr) and enantioselectivities (up to 92% ee). The catalytic cycle and stereochemical model were proposed by DFT calculation.